


this is just how we were taught to love

by alexisbldels



Category: Gilmore Girls
Genre: Alternate Universe - Canon Divergence, F/M, Friends to Lovers, chilton au
Language: English
Status: Completed
Published: 2020-03-19
Updated: 2020-08-11
Packaged: 2021-03-01 02:09:18
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 28
Words: 117,414
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23217541
Author URL: https://archiveofourown.org/users/alexisbldels/pseuds/alexisbldels
Summary: There's more than a crush here,Why aim to be crushed here?In which Jess attends Chilton, and Rory is set on learning more about her mysterious classmate.
Relationships: Rory Gilmore/Jess Mariano
Comments: 506
Kudos: 864
Collections: Best Gilmore Girl Fanfiction





	1. Pride and Prejudice

**Author's Note:**

> Other Characters/Pairings: Lorelai, Luke, Paris, Lane, Madeline, Louise, Emily, Richard, Liz, Dean. Lorelai/Luke (somewhat), Rory/Dean. 
> 
> Notes/Warnings: Begins in season 1 (or, the April before, in the first chapter). Flexibility with season 1 events and timeline. Smoking, drinking, sexual comments. 
> 
> Disclaimer: The title is taken from the song “Boys Like You” by dodie. Some of the plot follows season one happenings, but it diverges more or less completely eventually. 
> 
> Other notes: I'm really excited to be starting this fic! It's been in the works for a little while, so I'm glad I was finally able to start working on it. Like the last fic, updates will be sporadic, but hopefully the wait between chapters won't be too long. This, I'm hoping, will be better than the last, and more original, too. Thank you to Anabea and Kate for their help/patience with me being a little too mysterious when talking about it. I hope you guys enjoy, and thank you for reading.

The black BMW pulls into the Chilton parking lot and parks, but Jess’ stepfather makes no move to get out. His hand is still on the gear shift - for a quick getaway - as he glances over at Jess. 

“So, you know what to do?” He asks, no pretenses.

Jess nods. “Yep. Go in there, talk to Charleston, go to class. Not too difficult to remember, considering you’ve told me five times a day for the past week.”

“Don’t get smart with me,” his stepfather snaps. “And fix your collar. You can’t go in there looking like you’ve just worked a double shift at a McDonalds.”

“Have you ever even been to a McDonalds? They don’t wear ties there. Or blazers. And I thought you were the caviar type or something.”

“Jess.”

Jess clenches his jaw and reluctantly tightens his tie and fixes his collar, not making eye contact. “There. Better?”

“It’ll have to do,” his stepfather sighs, exasperated. “Charleston is a good man, Jess. Don’t be rude when you go in there, okay? I don’t want to have to clean up the mess later.”

Jess frowns. “You’re not coming in?”

“I told you, I can’t. I have a business meeting with Gehrman-Driscoll at eight.”

“You’re supposed to come in.”

His stepfather scoffs. “What, do you need me to hold your hand like it’s your first day of kindergarten?” 

Jess glances out the car window, watching students mill around the courtyard. “No.”

“That’s what I thought.”

“If Charleston gets mad, though-”

“It’s _Headmaster_ Charleston-”

“If he gets mad, what do I tell him?”

His stepfather purses his lips. “Headmaster Charleston and I are well acquainted. I’m sure he’ll understand; this is a very important meeting I have to attend.”

“Right,” Jess replies, emphasizing the t. He still doesn’t look over. 

“Your step-brother can take you back to the house after school. Your car won’t be fixed until tomorrow.”

Jess snorts. “It’s a cold day in hell when I get in a car alone with him.”

“There really is no need to be so melodramatic, Jess,” his stepfather scolds him. 

“Oh, but I disagree.”

“How are you going to get back, then?”

“I can take the bus.”

His stepfather’s eyes widen. “The bus.”

“Yeah, a bus. You know, those things where the wheels go round and round all through the town? And the wipers go-”

_“Jess.”_

Jess flinches at the sharpness in his stepfather’s tone. “I can take the bus. It’s fine. I did it all the time back in New York. It should be even safer here.”

“Fine.” The silver-haired man runs a hand over his chin, evidently in thought. “Look. I know-”

“Oh, great, a classic big talk,” Jess interrupts. “Can you wait a moment until Robert Reed shows up here with a camera crew?”

“For the love of god, shut your mouth for one second,” he snaps. “You really can’t go two seconds without giving me grief, can you?”

“Well, it is my favorite hobby. The infamous stepbrother, I hate to say, isn’t too bad at it either.”

“I know that you don’t want to be here, Jess, but I am simply respecting your mother’s wishes.”

“You couldn’t have waited to send me here until next year instead of mid-April?” Jess asks dryly.

“It wasn’t up to me. And you know we can’t exactly consult your mother about it now in her..condition. Now, what are you doing once you get out of the car?”

Jess takes a calming breath. “Go talk to _Headmaster_ Charleston.”  
“At least you’re not entirely incompetent.”

“Right back at ya.” Jess stretches a bit, overexaggerating a yawn. “Well, I’ll give him your love and all that.”

“Just get out of the car. I’m not getting any younger waiting for you.”

“Obviously,” Jess mutters. 

“What was that?”

Jess inhales sharply. “Nothing,” he replies, unbuckling and stepping out of the car. He grabs his messenger bag from the floor in front of his seat and slings it over his shoulder. 

“Don’t be home later than five,” his stepfather says, adjusting the rear-view mirror instead of looking at his stepson.

“What? No ‘have a good day at school, son?’” Jess quips.

“Are you quite done with the comedy routine? I have to go.”

Jess grimaces and shuts the door. His stepfather puts the car into reverse and drives away, leaving Jess standing on the curb.

Jess closes his eyes, takes a breath, and walks towards the iron gates. 

**

Jess feels incredibly out of place, walking down the corridor, surrounded by teenagers of varying wealth. He loosens his collar, hoping for just a little more oxygen; this place is suffocating already.

The headmaster’s office is behind two large white double doors. Jess pushes through, entering a small room with a secretary behind her desk. She doesn’t look up, even as the door swings shut.

“Hello?” Jess ventures, feeling uncomfortable.

The woman’s head snaps up, and Jess can’t help but think that she looks a lot like a vulture - a vulture with a chain on her glasses and hair pulled back so tight he can’t imagine she’s getting much oxygen to her brain. 

Jess swallows, hating this. “Jess Mariano. I’m here to see the headmaster.”

She glances down at a sheet on her desk before snapping her head back up again (jeez, you’d think she’d get whiplash doing that one of these days) and nods curtly. 

“One moment.”

She stands up, posture impeccable, and crosses the room to another set of double doors. She pushes the door open and walks in, leaving Jess standing there, alone. He fidgets slightly with the strap of his messenger bag until she walks back in, announcing, “Headmaster Charleston will see you now.” He remembers the first _Harry Potter_ book he read three years ago when his mother’s boyfriend at the time bought it for him, and wishes the childish thought would go away.

The woman holds the door open for Jess as he enters the office. A rather plump and balding old man with brilliantly white hair stands there, hand extended. Jess takes it and lets the man shake it, but drops his hand immediately after.  
“Mr. Mariano, I assume?” The headmaster asks congenially. Jess nods. “I’m Headmaster Charleston.”  
“Nice to meet you,” Jess says curtly. He looks around the room for a moment, feeling more and more uncomfortable each passing second.

There’s no one on the couch waiting for him as he takes a seat in one of the chairs facing the headmaster’s desk. The childish part of him wishes that there was some adult here with him - not his mother, not his stepfather, but _someone -_ but he rids himself of the thought.

Charleston sits behind his desk and looks directly at Jess. “So, Mr. Mariano,” he begins, putting on a pair of reading glasses, “you’re intelligent enough. Your teachers back in New York all said so. However,” he says, holding up a page of Jess’ transcript, “they all said you were ‘highly unmotivated, criminally rude, and rarely present,’ in some form or another. That cannot be the case here. We expect only the best here at Chilton, Mr. Mariano, and I hope you understand that.”

Jess’ jaw ticks. “Yes, sir.” It’s almost like a mantra these days.

“Not very talkative, I take it?”

“No, but something tells me this is going to keep going whether I say so or not.”

Charleston chuckles. “A sense of humor. We’re in need of that around here.”

“Glad I could contribute to the greater good.”

“You weren’t involved in any social activities back in New York,” Charleston observes, reading through Jess’ transcript. 

“Nothing interested me.”

“I see.” Charleston frowns. “Your teachers all say you were an avid reader, however,” he reads, sounding a little more intrigued than before. 

“Well, I know my phonetics.”

“Perhaps you’ll like our English classes here. Mr. Medina is a well-loved teacher - you’ll have him next year.”

Jess doesn’t quite make eye contact. “All due respect, sir, but I’m not really one to _enjoy_ being told what to read. Or classes, for that matter.”

Charleston sighs, folding his hands in front of him. “Mr. Mariano, I understand if you have had some - er - clashes with your schools before, but Chilton is the best of the best. You’re here for a reason, but you have to put in effort if you want to continue attending.”

Jess nods and does not reply.

Charles goes back to his transcript, skimming through it. “Do you have any aspirations, Jess? Any goals?”

“Well, I’d love to be out of here in time for lunch.”  
Charleston sighs again. “Maybe we should start simpler. What are your passions? You like to read - what can you tell me about that?”

“Give me a book and I’ll read it - as long as it isn’t Ayn Rand.”

“Not a fan of _The Fountainhead?”_

_“Atlas Shrugged_ doesn’t really do it for me, either.”

Charleston chuckles again in a way that really doesn’t seem all that authentic. “See, we’re starting to lean a little bit about you.”

Jess grimaces at the headmaster’s condescending tone. “I suppose we are.”

“What else do you enjoy reading? Proust, maybe? Pushkin?”

“Not really. Poe is okay, though.”

“You got anything in there, then?” Charleston asks, gesturing towards Jess’ bag.

Jess nods. “Austen.”

“Really?” Charleston asks, surprised. “Which one?”

_“Pride and Prejudice.”_

“Interesting. Not a lot of young men your age would be reading Austen - willingly, that is.”

“That’ll teach you to assume, now, won’t it?”

Charleston blinks in confusion for a moment before laughing. “Oh, another joke. You’re very witty, Jess, I’ll give you that.”

“Anyone who dismisses Austen because she’s a woman and writes about women shouldn’t be allowed anywhere near a library.”

“Very strong opinions, I see.”

“Just don’t have much patience for people dismissing good literature.”

“But still not a fan of Rand?”

“Not a fan of Rand,” Jess repeats.

Charleston smiles. “Anything else you’ve read? Maybe I won’t have read them - I’m in need of some recommendations, you know.”

Jess shrugs. “I don’t know. Anything by Nick Hornby is good. Or the Beats.”

“Oh, a fan of the Beats, eh?” Charleston muses. “I could never get into them much myself. Are you a fan of Kerouac, then?”

“You could say that.”

Charleston nods thoughtfully. “Well, then, you’re a reader. Have you ever thought of becoming a writer? Chilton has a wonderful creative writing program you can take starting as a junior. Or you could always join the literary magazine if you’re anxious to get to it.”

Jess stares at one of the busts the headmaster has around the room. “I haven’t really thought about it.”

“Well, consider it, will you?” Charleston says. “Everyone here has promise, Jess. I’d hate to see any of my students waste the many opportunities that Chilton offers.”

“I’ll keep that in mind, then.”

Charleston’s expression becomes a bit more serious as he shifts in his seat. “Jess, I have known your stepfather for a while now. He’s investing a lot into sending you to this school, you know?”

“He’s mentioned it once or twice.”

“Chilton has one of the highest academic standards of any school in America. You’re a smart kid, Jess, but you’re beginning your academic career here at Chilton on thin ice already. I am perfectly content to discuss literature with you, but I don’t want to have to call you in here often. Now, I understand that you are starting late in the year, and aren’t used to the highly competitive atmosphere here at Chilton. We’ll be lenient for the rest of the school year so you can adjust, but starting next semester, we expect only the best from you, Mr. Mariano. You’re on the ledge already; failure isn’t an option for you. Do you understand?”

Jess’ jaw tightens. “Yes.”

“Your grades at your old school won’t have an impact on your ability to graduate Chilton, but if you continue with the patterns you kept in New York, I will have no choice to expel you. Do I make myself clear?”

“Yes, sir.”

Charleston suddenly smiles again, the dangerously serious atmosphere fading away. “Take this to Miss James in the administration office across the hall, then,” he instructs Jess, pushing Jess’ transcript file across the desk. “And have a good first day at Chilton.”


	2. Great Expectations

**Summary for the Chapter:**

> Rory has her first day at Chilton, but finds herself struggling a lot more than she expected.

**Notes for the Chapter:**

> I guess a stay at home order is doing wonders for my productivity when it comes to writing this...but I'm not complaining about getting this written.  
> NOTE: Some dialogue is taken from 1x02 of Gilmore Girls - it's a minimal amount, because I hate just copying the dialogue from the show, but it's necessary for the story.  
> I would also like to clarify that I don't like Max in the show that much (he was boring) but he's different in this fic.

Chilton isn’t what she expected. If Rory’s being honest, she’s not really sure _what_ she expected, exactly, but she feels kind of stupid being disappointed. And it’s not that she’s new to disappointment - nearly sixteen years with a flakey father teaches you what it is fairly quickly - but now she knows that she was fooling herself thinking life at Chilton would be as easy for her as it was at Stars Hollow High. 

Charleston’s words keep replaying over and over inside her head as she moves from class to class. _Failure is a part of life, but not a part of Chilton._ She can’t fail. Failure isn’t part of who Rory Gilmore is. And her mom and grandparents have put so much into her education already; she can’t let it be a waste, she just can’t.

She’s so behind already, so lost; the girl named Paris is _so_ good, _so_ smart, answers every question like rapidfire. Is this what the standards are? Can she even level up? For one of the first times in her life, Rory is beginning to doubt her academic skills. Maybe she’s just too _stupid_ to be here.

It was easier, back in Stars Hollow, when all she needed was Lane. It didn’t even matter that the other girls painted their nails in class and whispered about her right in front of her. She had one friend, and she had her books; that was all she needed.

But now - now, it’s different. Paris hates her, for whatever reason, so she’s made an enemy, already, somehow, and who will she get those notes from, anyway? (Is she even going to be able to catch up? Childish as it is, Rory misses Lorelai. She could use a hand to hold right now.)

The way the boy named Tristan looks at her makes her feel uncomfortable in her own skin. And not in the good way, either - not in the way _Dean_ makes her feel. Dean. That was the boy she almost threw this all away for, right? Maybe that would’ve been the right decision. She’s a little too overwhelmed one class in for this to feel like a good decision.

Failure is something Rory has been afraid of for as long as she can remember. And now, she feels like she’s hurtling towards rock bottom with no one to help her. She doesn’t want to be Mary, or Paris’ enemy, or anything else other than _Rory._

Regret. It’s a funny thing, isn’t it? This - the thing she’s been working towards for god knows how long, is becoming one of her biggest regrets yet.

Yeah. It’s just hilarious. 

**

“My locker - it just slipped. I pulled too hard. I didn’t mean to - is there water in that moat?”

“Get away from me.”

Rory helplessly watches Paris storm away, feeling the pit in her stomach grow exponentially. She closes her eyes and takes a deep breath, her exhale shuddering. _It’s going to be okay._

She grabs her books from the floor and shoves them in her locker. _No, it’s not._

Closing her locker, Rory adjusts her bag and turns around, and finds herself facing a boy that she hasn’t noticed yet today. He’s got dark, curly hair, a messenger bag, and a look in his eyes that she can’t quite identify. 

“What are you looking at?” She demands, crossing her arms across her chest. 

He raises an eyebrow. “So, you broke Paris Geller’s project, huh?” 

Rory glares at him. “Well, obviously you were right here and saw it all happen, so I think I’ll let you answer that for yourself.”  
He holds his hands up in surrender. “You’re right. My bad.”

“What do you care, anyway?” Rory snaps. 

“Nothin’. Just...good luck,” he responds. “Breaking Paris Geller’s project...you’re gonna need it.”

“Gee, thanks.”

“No, I mean it, I mean...she’s not someone you want to be on bad terms with.”

Rory tries to make her glare even more vicious. “I think I could’ve figured that out for myself, thanks.”

The boy smiles - smirks, more like it - and straightens up. “Just trying to help. You’re new, right?”

“Yeah,” Rory mumbles, staring down at her shoes instead of making eye contact with him.

“Where’re you from?”

“None of your business.”

“Fair enough.” The boy looks around them for a moment before he speaks again. “What’s your name?”  
“Oh, so you can just ignore it and call me Mary instead?” Rory retorts angrily. “No thanks.”

“That’s not really my style.”

“Oh, and making fun of me for one of the most embarrassing and possibly life destroying interactions of my life is?”

The boy frowns, like he’s trying to figure her out. Well, good luck, because she’s not about to let him. “First off, I’m sure you’ll get past this incident. Second of all, I’m not-”

 _“‘Good luck?’”_ Rory demands. “Yeah, that just _reeks_ of sincerity.”

The boy relents, leaning back up against the wall. “I meant it. Good luck - you’re really going to need it.”

Rory scowls at him and storms off without another word. She turns the corner, dread building when she realizes she doesn’t even know where her next class is. She looks behind her, but the boy didn’t follow her - he must’ve gone off to his own class. She groans and turns back around, running right into a man that she recognizes as her English teacher.

“Mr. Medina - oh my God, I’m so sorry,” she stammers, trying to hang onto whatever is left of her dignity.

He smiles kindly. “No worries. First day jitters, right?”

“Something like that,” she admits. 

“The bell rang already,” he notes, looking up and down the hall. “What class do you have right now?”

“History. With Mrs. Ness. But I don’t know - I don’t know where it is, and I’m running late anyway because I bumped into Paris and broke her project - broke her _project,_ can you believe my luck? _-_ and then this _guy_ was giving me a hard time for it, and I-”

“Rory, Rory, breathe,” Mr. Medina chuckles. “Your class is that way,” he says, pointing in the direction she was coming from. “Room 204.”

“Oh.” Rory frowns. “Thank you.”

“Don’t worry about being late, either,” Mr. Medina says, reaching into his bag. He pulls out some paper and a pen. “You were just having a talk with me about ways to catch up in my class quicker, and we lost track of time,” he says, scribbling down on the paper. 

He offers it to her and she takes it, looking down at the writing. “Thank you, Mr. Medina. And sorry, again, for this.”

He smiles. “Don’t worry about it.”

“Paris is going to kill me,” Rory laments. “I broke her project. Can you believe that?”

“I think we have enough teachers around to make sure that won’t happen.”

“She’d find a way. Have you met her?”

Mr. Medina chuckles again. “It’ll smooth over sooner or later. Now get to class, okay? You don’t want to miss even more material.”

Rory nods. “Okay. Thank you, again.”

Mr. Medina nods. “Have a good day, Rory. I’ll see you tomorrow.” 

“See you tomorrow.”

Rory turns around and rushes towards her class, hoping against hope that Paris won’t be in it. God, right now, even Tristan creeping her out and calling her Mary would be preferable than facing Paris’ wrath. 

**

In hindsight - no, in hindsight, she wouldn’t have done any differently. Trying to save Paris from the teacher’s wrath might’ve looked stupid and reckless to anyone else, but at least _trying_ to divert the blame was worth it. She’s Rory Gilmore. Who would she be if she didn’t try?

She sits back down in her seat, hating the feeling of everyone’s eyes on her. A great way to introduce herself, right?

God, will this hell of a day ever be over?

**

Turns out, relief comes a little quicker than she anticipated. 

Rory has never really been the type to pass notes, even as an olive branch, but Paris crumpling it up and throwing it on the floor is the final straw. She was only trying to help and make up for her mistake - now, all bets are off.

“‘The Romanists, with great adroitness, have built three walls about them, behind which they have hitherto defended themselves in such wise that no one has been able to reform them; and this has been the cause of terrible corruption throughout all Christendom.’ Who said this?” Mrs. Ness demands, surveying the class.

Rory catches Paris leaning forward, ready to answer, but she _knows_ this, she does, and why waste an opportunity to impress?

“Martin Luther,” she blurts out before Paris can answer.

“Very good, Miss Gilmore,” Mrs. Ness says. “And what year did Martin Luther address the Christian nobility?”

“1520,” Rory answers quickly, beating Paris to the punch again.

“Very good, Miss Gilmore.” The bell rings. “Until next time, class.”

Rory starts to gather her things, but when she looks up, Paris is leaning over her desk with a murderous expression on her face. 

“Stay out of my way,” Paris threatens. “I will make this school a living hell for you.” And with that, Paris turns on her heel and leaves the classroom.

She doesn’t even get a chance to breathe before Tristan smirks at her. “See you tomorrow, Mary.”

“The name is Rory,” she mutters, standing up and leaving the classroom.

Rory turns towards her locker, but bumps into yet another person who seems to appear out of nowhere. “Oh, _jeez.”_

The boy from earlier frowns at her and takes a step back. “You good?”

She glares at him. “What is it now?”

“Good job, Gilmore,” he says simply. “At beating Paris to those questions. Not many people would have the guts to attempt that.”

Rory scowls. “Do you get tired of making fun of me, or what?”

“Making fun of you?” He repeats, confused. 

“Drop the act. I don’t buy it for a second. Are my issues with Paris just that entertaining to you?”

“Entertaining? No. Amusing? Not really. Empowering? Well-”

“Okay, you can stop now, thank you,” Rory says, pushing past him to get to her locker. To her relief, the boy doesn’t keep talking to her. He starts to go in the other direction, but out of the corner of her eye (remember, she couldn’t care about him less, so she’s _not_ paying any attention to him) she sees Tristan stop him.

“Get out of my way,” the boy says flatly, trying to sidestep him, but to no avail.

Tristan cocks his head to one side condescendingly. “Come on, Jess. Don’t be hostile.”

 _Jess. So his name is Jess._ “Just let me get to my locker, then,” he says through his teeth. People continue to mill around the pair, paying them no mind.

“But it’s so much more fun to mess with you a little.”

“Get out of my way,” Jess repeats. “I’m not doing this again.”

“Not doing what?” Tristan says in a mocking tone.

Jess clenches his jaw. “Fighting you.”

“That’s all people like _you_ are good at,” Tristan shoots back, disgust in his voice. 

Jess’ expression is unwavering in its composure. “People like me.”

“You don’t even want to throw one punch?”

Jess glances behind him, and Rory quickly averts her eyes. “What I want is a whole other story, Tristan. Just drop it.”

“Fine.” Tristan steps aside, hands up in mock surrender. “Say hi to your daddy for me, would you?”

Rory watches as Jess grabs his jacket and slams his locker shut. He storms past her, not before muttering, “What’re you looking at?” in her direction.

Rory blinks a couple times, bewildered. Overall, today has been a pretty crappy day, but this is just...odd. But she doesn’t like Jess, she decides, even if Tristan _was_ giving him a hard time. He made fun of her _twice_ today and she isn’t going to stand for that. 

Rory closes her locker and shoulders her bag; for a moment, she stands still, and then walks down the hallway towards the parking lot.

**

When she’s finally home, Rory collapses back on her bed, too tired to even take her stockings off.

“Hey, Rory - Pizza or Chinese?” Lorelai calls from the kitchen.

Rory presses a hand to her temple and closes her eyes. “Pizza, please.”

“Okay. But just be warned, I’m getting a _lot_ of garlic bread, too.”

“As long as you share.”

“No promises!”

Rory groans and sits up, slowly toeing off her shoes and kicking them to the side. Today was by far one of the longest days of her life. But at least she has an ally in Mr. Medina, and who knows - maybe she’ll find a friend. Now that she’s out of the woods for the time being, she feels just a little bit lighter.

Rory sits down at her desk and pulls out her textbook and gets to work. She’s not giving in - not yet.

**Notes for the Chapter:**

> Stay home and wash your hands!


	3. The Professor

**Summary for the Chapter:**

> Rory turns to Mr. Medina for help, and Jess ignores his advice.

**Notes for the Chapter:**

> Another update? Already? I don't know how I've updated consistently for three chapters, but I'm not going to get used to it. That being said, I hope this motivation stays, because I'm really enjoying everyone's feedback and reactions to my updates.  
> I hope you enjoy this one, too; it's longer than the last two were, which is always nice. I'm really happy with this one, so I hope you guys are, too!

One week in, and things are getting a little easier. Paris still hates her, yes, and Tristan is still...Tristan, but at least she’s catching up, and a nice, quiet girl gave her the notes that she needed, so overall, things are looking up.

Jess hasn’t spoken to her since that fateful first day, and Rory takes it as a good sign, too; she doesn’t need more people to give her a hard time. She does that enough on her own already.

She can’t help but wonder _why,_ though. It’s not that she cares, because she doesn’t, not really - it’s just that he made the effort to speak to her twice and now, nothing. And there’s something weird going on with him and Tristan. Something that she’s sure originated before she started attending.

He’s just a little mysterious, Jess, and Rory finds herself intrigued. Chalk it up to her being a journalist, or her natural curiosity, but she wants to know just a little bit more about him. 

(That being said, she likes it the way it is between them - a complete lack of communication.)

**

Mr. Medina begins class by handing back their essays, a grade she’s been waiting rather anxiously for, and she feels the familiar excitement when he stops by her desk. 

“Miss Gilmore,” he begins, and she sits up, ready for praise. “Take these home,” he continues gently. “Learn from your mistakes.”

She looks down at the paper, and her stomach drops. A ‘D.’ She’s never gotten a ‘D’ before in her _life._ Rory barely listens to what Mr. Medina is saying - to err is to be human, they beat that out of you, or something - she can’t focus on much else but the big red ‘ _D’_ on the top of her paper. She can’t believe it, not at all. She’s a writer. How did she get a ‘ _D?’_

“Okay. Next up, the test - the dreaded test,” Mr. Medina continues. “Shakespeare - the man we’ve been droning on about for the last three weeks - finally comes back to haunt us on Friday. This is a big one, my friends - multiple choice with an essay section that will count for twenty percent of your grade this semester.”

Rory swallows nervously. _Twenty percent?_

“Don’t be fooled by my kind face and charming personality. This test will be hard, and there will be no make-ups.” The bell rings, but Rory is frozen in place. “Refer to the study materials that I gave you at the beginning of the month and those extensive notes I know you’ve been taking. Mr. Mariano, can you hang back for a second, please?”

Rory moves slowly, as if in a trance. She can vaguely hear Paris talking to Madeline and Louise, but doesn’t pay attention to their bragging until Paris stops in front of Rory’s desk with an air of superiority that is already _way_ too familiar.

“A ‘D,’ however, would be cause for concern,” Paris says loudly, looking down at her. 

“A cry for help,” Madeline adds.

“A job application for McDonald’s.”

“Would you like fries with that?”

Rory spins on her heel to face them. “Stop it.”

“Hey, you know, not everyone can be smart,” Paris says condescendingly.

“I’m sure if you keep tag teaming you could write a whole routine.” Rory retorts. “Louise, you have anything particularly witty to add? Your comedic genius could save the whole act.”

Paris raises an eyebrow. “We’re only showing concern, Rory. Maybe you’re just...not cut out for this school.”

Rory opens her mouth to retort, but Paris, Madeline, and Louise are already walking away. She curses silently and walks towards the front of the room, holding her paper close to her chest. Jess is still here - oh, so _he’s_ Mr. Mariano - and when she walks past him, face burning red, he says, “Wait.”

She stops and turns to face him. He has a disheveled look to him, she notices - loose tie and a collar that isn’t fully buttoned, and his sleeves are rolled up half-hazardly. He fidgets with the strap of his messenger bag as he looks at her. 

“That essay was stupid, anyway,” he offers with a shrug. “Don’t let Geller get to you.”

Rory frowns, a little confused - isn’t he supposed to be a jerk? She opens her mouth, but is saved from saying anything when Mr. Medina speaks.

“So, Mr. Mariano, you - Miss Gilmore,” he says in surprise upon seeing Rory. “Do you need something?”

“It can wait,” Rory says hurriedly, glancing over at Jess. 

Mr. Medina smiles. “Nonsense. Mr. Mariano, you don’t mind waiting a moment, do you?”

Jess shrugs. “I’ve got nowhere to be. Go for it.”

“Thank you. So, Rory, what’s going on?” Mr. Medina asks, taking a seat behind his desk. Jess wanders to the back of the classroom, out of earshot.

“My essay,” Rory says, holding out the paper. “You gave me a ‘D.’ And I just...I don’t really understand why,” she says lamely. 

Mr. Medina nods thoughtfully. He accepts the paper from her and skims through it. “You’re a good writer, Rory,” he says. “That’s not a doubt. However, your structure was poor, and your arguments weak. See, here,” he says, pointing to one section where _how does this connect?_ is written in red pen, “your topic sentence for this paragraph is really strong. Your evidence is solid, but when you go to connect the evidence to your argument, you _explain_ the evidence more than argue your point. You with me so far?”

Rory nods.

“Same thing in the second paragraph. You wrote here, ‘Romeo’s love for Rosaline proves itself to be an immature infatuation more so than love,’ and your quotation would back this up without a doubt. But then you go to say that ‘Romeo says that Rosaline has sworn off of men, and that is the source of his depression.’ Yes, that’s true, and it’s good to describe your evidence, but it’s not an argument for _how.”_ Mr. Medina looks back up at Rory. “So, with this feedback, what would your _reasoning_ be?” 

Rory hesitates. “Because Romeo is reacting in this way...in a really dramatic, all-or-nothing way...it - it portrays his childish beliefs about love. And...and because he has no actual relationship with Rosaline, he...sorry, I don’t - I don’t know,” she says, biting her lip.

“No, no, you’re doing good. Keep going. You know this.”

Rory frowns. “The lack of an actual connection or substance to their relationship proves that he, uh...that Romeo is in love with the _idea_ of Rosaline, as opposed to his relationship with Juliet, which-”

“Don’t forget to stick to your topic sentence,” Mr. Medina reminds her. “But you’re on the right track. You’re able to do this, Rory, and I’m sure on the next paper, you’ll do better. Just keep this in mind, okay? Read over the notes I’ve written, and keep the criticisms in mind for next time.”

“Is there anything I can do to improve my grade?” Rory asks anxiously. “Extra credit work, or-”

Mr. Medina shakes his head. “I’m afraid not. However,” he continues, seeing the crestfallen look on Rory’s face, “how about this. Read over my notes, rewrite the paper, and we can go over it at some point this week. It won’t give you any extra credit, but it’ll help you improve your future papers, and hopefully help you study for the test on Friday.”

Rory nods. “Okay. Thank you.”

He smiles. “Don’t worry too much about it, Rory. This is something a lot of students struggle with at first.”

“I know, but I’m supposed to be better,” Rory laments, not caring how she might sound. “I got into Chilton for a reason. And everyone here is so advanced, and I just…” She trails off, not wanting to cry in front of her teacher.

“I understand, Rory, I do,” Mr. Medina says gently. “But you don’t need to worry just yet. You’re a bright student, and one ‘D’ isn’t the end of the world. Okay?”

Rory accepts her essay back from him and smiles weakly. “Okay.”

He smiles. “I’ll see you tomorrow. Mr. Mariano, can we talk?”

Rory thanks him again and exits the classroom. She’s about to walk away when she hears Jess’ voice, and her curiosity gets the better of her. She stands against the wall where neither of them can see her, peeks through the doorway, and listens.

“What did you need to talk to me about?” Jess asks, jaw set.

Mr. Medina sighs. “Pull up a seat. We need to talk about your essay.”

Jess does as he is told and sits down. Mr. Medina looks down at a paper he is holding. Even from where she is, Rory can see the large red ‘F’ on the top of the page. 

“Do you know why I want to talk about your essay?”

Jess shrugs. “I got an ‘F.’”

“You did.” Mr. Medina sets the paper down on the surface of the desk. “But I’m not obtuse. I know talent when I see it. And you, Mr. Mariano, are very talented.”  
“But I got an ‘F.’”

Mr. Medina gives Jess a wary look. “I can tell when a student fails an assignment on purpose, Jess. I’ve been in the game for a while, and I thought I’d seen all the tricks, but I have to say, you found a way to surprise me.”

“What do you mean?”

“To get an ‘F,’ you could’ve skipped the assignment altogether. But you didn’t. I especially enjoyed the rather, uh, _detailed_ description of my teaching method in the second paragraph. Oh, and the little anecdote about aliens abducting Romeo and Juliet on the last page. It was very creative.”

Rory holds back a laugh. As much as she likes Mr. Medina, the whole idea _is_ kind of funny.

Jess fidgets a bit in his seat, but he doesn’t say anything.

“Here’s the thing, Jess,” Mr. Medina continues. “You’re smart. You might not want to admit it, but you are. You’re definitely qualified to be at this school, but your grades don’t reflect it.”

“So why not kick me out?” Jess mutters.

Mr. Medina sighs. “I understand that you don’t want to be here. Maybe education isn’t your thing. But I want you to try, Jess. You’re too talented to let it go to waste.”

“I thought you said you enjoyed it.”

Mr. Medina chuckles. “I did. It was entertaining - but that’s not the point of the assignment. Now, this prompt isn’t very hard, especially not for you. Forget evidence - I’ll even give you the thesis. Tell me why Romeo’s love for Juliet is more authentic than his love for Rosaline.”

Jess remains silent.

“Just one reason. That’s all I’m asking.”

“Was it, though?” Jess mutters.

Mr. Medina frowns. “What?”

Jess fidgets, clearly uncomfortable. “Was it? They were both kids, and he killed himself without making sure she was actually dead. That doesn’t scream rational and mature to me.”

“Why not?”

Jess’ eyes narrow. “I know what you’re doing.”

“You could write this paper better than anyone else in this class, Jess, and I think you know it,” Mr. Medina says calmly. “This isn’t hard for you.”

Jess scoffs. “How the hell do you know what isn’t hard for me?”

Mr. Medina doesn’t reply. He takes his red bed and pushes Jess’ paper towards him. “You can still turn things around, Mr. Mariano. You’re a natural author. It wouldn’t take much from you to turn this-” He draws a line on the side of the ‘F,’ “-into this.”

Jess stares down at the ‘A.’ “I don’t know what you’re talking about.”

Mr. Medina sighs. “Okay, Jess. I’ll see you in class tomorrow.”

Rory presses her back against the wall, head swimming with thoughts.

Maybe, just maybe, there’s more to Jess than she originally thought.

**

Rory walks through the courtyard quickly, trying to get out the iron gates without so much as a word to another person. Apparently, her luck ran out a while ago, because she’s stopped by Tristan before she can leave.

“What do you want, Tristan?” Rory demands. 

The boy smiles mischievously in a way that makes her skin crawl. “Not much. Just wanted to see how you were doing, you know, with that ‘D’ and all.”

“Great, so everyone knows, huh?”

“Not necessarily. I just...have my ways, you know?”

Rory refuses to make eye contact. “Anything else?”

“Well, how do you know I won’t tell more people?” Tristan says innocently. “Maybe you can do something for me, you know, just to make sure.”

Rory grimaces. “Like what?”

“Go on a study date with me.”  
Rory almost blanches. _“Excuse_ me?”

“C’mon, _Mary._ We both obviously need to study for that test on Friday, so…”

“Not going to happen,” Rory says through gritted teeth. “I really need to catch my bus, so _leave me alone.”_

Tristan holds his hands up in surrender and backs up. “Okay, okay. See you tomorrow, _Mary._ And reconsider!” He calls after her as she hurries away from him.

“Why won’t he just leave me alone?” She mutters to herself. "What is he getting out of this?"

She doesn't really want to know. 

**

Going over her revised paper with Mr. Medina was definitely helpful, but cramming the night before the test couldn’t hurt, Rory figures.

Turns out, it can.

She _never_ oversleeps, she’s always punctual, always - but today just has to be the fluke. Rushing to school, driving as fast as she can while still being safe, and getting hit by a deer. Everything is going wrong. 

She’s going to be late. She’s going to be late for a test that is worth 20% of her grade. That and the ‘D’ she received on her paper are one surefire way to make sure she doesn’t get into Harvard.

She feels a little guilty, blowing up on Mr. Medina like this once she finally gets to class, but he’s being _unfair,_ if he would just _listen-_

It’s also admittedly very satisfying to tell off Paris - “Just what is wrong with you, huh? You have everything! You have the grades and the status! What is wrong with you that you have this constant need to be the biggest jerk in the world? Huh? What’s up? What’s up, Quippy? Why so silent?” - and to yell “And for the last time, the name is _Rory!”_ in Tristan’s face. It didn’t wipe that obnoxious smirk off his face, but at least it’s a start.

As she waits for her mother outside of the principal’s office, Rory stares down at her shoes, face burning red. She feels better, getting it all out of her system, and she doesn’t regret it, not really, but now all the attention is back on her (not that it ever left). Whatever. All she can do is wait for her mother to be done and see if she’s been expelled or not.

(She’ll still worry about it, though. All she does is overthink, it feels like.)

“Looking for an escape route?” 

Rory sits up, and who else is it but Jess. She must’ve been zoned out, but here he is, sitting next to her on the bench. “What?”

“You’re staring at the floor really hard,” he says, gesturing to the tiles. “I was wondering if you were searching for a loose floorboard or something. Like in _Clue.”_

She glares at him. “Okay, bye.”

“I liked what you said earlier.”

She blinks a couple times, confused. “What?”

“What you said. Your whole blow up,” he explains. “It needed to be said.”

She frowns. “Which part?”

“It’s ridiculous that they wouldn’t let you take the test,” Jess continues. “I mean, what is Mr. Medina’s _problem?_ You’d think staying up all night to study for _his_ test would just boost that man’s ego through the roof.”

“Don’t give him such a hard time,” Rory says angrily. “He was just doing his job. All I did was make a scene.”

“Maybe so, but you had every right.”

“They’re going to kick me out,” Rory groans, putting her face in her hands.

“No, they’re not.”

“How do you know that?”

“Because I’ve pulled the fire alarm twice and I’m still here.”

Rory sits up and frowns at him. “I can’t tell if you’re serious or not.”

“You were right, anyway,” Jess says with a shrug. “Paris is wrong to be singling you out.”

“Yeah, well…”

“And Tristan,” Jess says with a sneer. “God, put him in his place more often, will you? It’s cathartic.”

Rory laughs through her nose. “Well, I’ll try.”

The corner of Jess’ mouth quirks up. “Appreciated.”

“How did you get here, anyway? Don’t you have class?”  
“I snuck out.”

 _“What?”_ Rory asks, bewildered. “How?”

“I doubt Ms. Tailor misses me much from 3rd period math. She never looks up from that textbook of hers. I don’t think she’s looked up from that thing _once_ in her entire career.” 

“Oh, that’s true, she doesn’t.” 

“Besides,” Jess says, “I couldn’t let you leave without telling you how much I admire you for that outburst, could I?”

Rory just groans and puts her head in her hands again. “God, I am never going to live this down.”

“Probably not. Not until your next blow up, anyway.”

She gives him a look. “Hilarious.”

“I try.” There’s something playful in his eyes as he looks at her.

“Why are you suddenly being all nice to me?” She blurts out after a pause.

Jess frowns. “What do you mean?”

“Well, my first day, you made fun of me _twice,_ then you didn’t speak to me for a week, and now-”

“I wasn’t making fun of you. I meant it - good luck is always needed when dealing with Paris Geller. Besides,” Jess adds, “why would I make fun of you on your first day? My moral code says to wait about a week first.”

“Oh. I guess I just - assumed. Sorry,” she adds guiltily.

Jess shrugs. “No biggie.”

“Can we start over?” She asks sheepishly.

He half-smiles again. “Sure. Jess Mariano,” he says offering his hand.

She takes it and shakes it. “Rory Gilmore. Pleased to meet you.”

“Nice to meet you, too, Miss Gilmore.” 

They drop their hands. “So, you hit a deer?” Jess asks after a moment.  
“No, I got hit _by_ a deer.”

“How does that even happen?”

“These things seem to happen to me.”

Jess shakes his head in amusement. “That’s...kind of funny, actually.”

“Hey, no, it’s not,” Rory retorts, elbowing him lightly in the side, although, she has to admit, it _is_ kind of comical.

“It’ll amuse you some day.”

“Not if I fail this class.”

“Nah, you won’t. Medina doesn’t have a mean bone in his body. Intrusive ones, yes. Nosy ones, yes. Mean? No.”

“Hey, what happened to him boosting his ego?”

“Things change. Keep up, Gilmore.”

The doors open, and a disgruntled Lorelai walks out. “Alright, Rory, let’s just get on the road and go - oh, hello,” she says, cutting herself off. 

“Mom, this is Jess. Jess, this is my mom,” Rory says, gesturing between the two.

“Nice to meet you,” Lorelai says, sounding confused.

“Likewise,” Jess says.

Lorelai blinks for a couple seconds. “Alright, let’s just...go home. And you can tell me about what it’s like to get hit _by_ a deer, ‘cause for the life of me, I can’t figure it out.”

“Gladly.” Rory stands up and grabs her bag. “Bye, Jess.”

“See you.”

Rory smiles to herself as a bit as she walks to the car with her mother. After her mother marvels at the antler prints and they look for the deer, Lorelai asks, “So, what happened to Dean?”

“What do you mean? He’s still in Stars Hollow last I checked,” Rory answers confusedly. “Did something happen that I don’t know about? The mafia finally took over?”  
“No, I mean, what’s going on with that Jess kid?” Lorelai asks. “I don’t have any issues if you don’t like Dean anymore, but the least you can do is keep me updated. The inn can get rather dull, you know.”

“Not as long as Michel is there,” Rory reminds her.

“Touché.” 

“And I still like Dean,” Rory says, somewhat defensively. “Jess is just...a classmate. Hell, I didn’t even _like_ him until today because I thought he made fun of me on my first day, but it turns out it was just a misunderstanding.”

“Must be nice to have options,” Lorelai laments. “All I have is an empty answering machine and an angry french coworker.”

“Hey, I do not have _options.”_

“Shh. We’re talking about Mama now!”

“Just as long as I don’t have to justify who I like anymore.”

“Maybe Headmaster Charleston is looking for a mistress…”

“Gross! Mom!”

**

When Lorelai informs Rory about the voicemail from Mr. Medina, saying that she can do extra credit work to make up for the test, Rory takes it as a sign that things can only go up from here. On Monday, she gets to school early to thank Mr. Medina, but before she walks in, she sees Jess, sitting and talking to Medina once again. She stops cold in her tracks and listens. 

“Alright,” Mr. Medina says, “nice to see you so bright and early on a Monday morning, Mr. Mariano. I believe that the two of us need to have another chat.”

Mr. Medina places a scantron on his desk and pushes it towards Jess. “You know what’s odd about this?”

“No, but I assume you’re about to tell me.”  
“Zero percent,” Mr. Medina says. “Do you know how many students of mine have ever scored that on this test? None. Even with four answer choices on each question, there’s a hundred questions - if you guessed randomly, you would still get 25% correct. The only way to get a zero is if you knew most, if not all of the answers.”

“Huh.”

“And your essay section was particularly inventive. I see you ditched the prompt all together and wrote a very harsh film review for _The Matrix.”_

“So, what are you saying?”

“I know you failed this on purpose,” Mr. Medina says calmly. “Just like your paper. Now, I don’t know why you’re doing this, but if you need help, ask for it. It doesn’t need to be me - maybe ask one of your peers. But I’m not going to have patience for much longer, Mr. Mariano. I’m perfectly happy to help you, but I can’t force you to succeed. That’s completely up to you.”

Jess’ jaw ticks as he looks down at the scantron. He doesn’t say a word.

Mr. Medina looks at Jess wearily. “I’ll see you in class, then.”

Jess wordlessly stands up and leaves the classroom, not even bothering to put his chair back. Mr. Medina sighs and stands up, putting Jess’ chair back behind its proper desk. Rory tries to process the conversation she just heard.

She’s unsure why Jess is so averse to doing well in school - she doesn’t know him well, not at all - but she assumed that everyone at Chilton would be an overachiever like her. Why is he here at all, then? 

And why hasn’t he left?

**Notes for the Chapter:**

> Comments with your thoughts and/or theories are always appreciated! Thank you for reading <3


	4. Much Ado About Nothing

**Summary for the Chapter:**

> Rory and Jess work on an assignment together. Rory tries to learn more about him, but her efforts are more unsuccessful than she would like.

**Notes for the Chapter:**

> Thank you guys for all the comments you've been leaving! Half of the fun is seeing your reactions, so please keep leaving them!  
> Also, fuck Tristan Dugray lives <3 enjoy!

“The Great Gatsby,” Mr. Medina says. “A classic work of literature. And something you all should have finished reading for homework last night. In addition to our usual class discussion over the novel, I am also assigning a project just to make sure you actually read it. Cliff’s notes won’t save you now - this requires you to actually _think.”_

He smiles when a handful of students groan. “I’m loving the enthusiasm. Unfortunately, this is _not_ optional - and will be worth a fair portion of your grade. This will be a group assignment-”

“Can we choose our groups?” Tristan asks from the back of the classroom. Rory shifts uncomfortably, sure that his eyes on her. Almost as confirmation, Paris shoots Rory a glare. 

“Yes, you can choose your own groups. However, there can only be two people per group,” Mr. Medina adds before excited chatter can begin, “and I want you to make sure you’re working with someone who you can actually be productive with. There will be peer review, and you don’t want to risk a bad grade. Any more questions about groups, or can I continue?”

The class is silent, so Mr. Medina continues. 

“With your partner, you will create a series of four letters between two characters of your choice - two letters each - excluding Nick. This needs to reveal a side of the story that Nick would not be able to know. These will not be presented-” A sigh of relief fills the room. “-however, I still expect the same level of quality as I would any other assignment. You have until next Friday to complete this. Any questions?”

No one raises their hand.

“All right,” Mr. Medina says, clasping his hands together. “The bell should be ringing about...now,” he says as the bell rings. “Don’t forget to work on the assignment! And feel free to ask me any questions.”

Rory zips up her bag and slings it over her shoulder; as she does so, she accidentally makes eye contact with Tristan. _Great._ She can’t do much but steel herself as he approaches her. 

“So, Mary, you have a partner yet?” He asks with a cocky grin.

Rory grimaces. “No, not yet,” she admits. She’s given up on the _Mary_ front for now. 

“That works out well.”

“And why is that, Tristan?”

Tristan’s smile widens. “I was thinking that we could work together. And you can’t say that this is a solitary activity. You have to have a partner; it’s required.”

“Oh. Well, uh…” Rory trails off, trying to think of an excuse. “I don’t…”

“You don’t have a partner...I don’t have a partner...sounds like a match made in heaven, right?”

“One would think,” Rory mutters, holding her books closer to her chest, wishing she could disappear on the spot. 

“So, then, it’s decided, right?”

Rory opens her mouth to retort, to say _anything_ to get out of this, when Jess seems to appear out of nowhere. 

“Hey,” he says to her. 

“Hey,” she says, surprised. “What’s up?”

“Do you have a partner for the project yet?” He asks.

“Well, actually-” Tristan starts, but Rory cuts him off.

“I don’t,” she says with a hint of a smile. 

Jess ignores the look Tristan is giving him. “Do you want to work on it with me?”

Rory smiles, relieved. “I’d be up for that.”  
“Great.” Jess shoots Tristan a look that she can’t quite read before he looks back at her. “Meet me in the library after school?”

“Sounds good to me. Walk me to my next class?”

“I think we’re heading in the same direction, yeah.”

The pair walk out of the classroom. Once they’re out of earshot, Rory lets out a sigh of relief. 

“Thank you, thank you - you have _no_ idea what you just did for me.”

Jess shrugs. “Was the least I could do. You shouldn’t have to spend more time with him than what is absolutely necessary.”

“So, you asked me to work with you just because you didn’t want me to work with Tristan.”

“No one should have to put up with him on a daily basis. Trust me, I know that from experience,” he snorts. “Besides, you looked more uncomfortable than I’ve ever seen anyone look in my life.”

“Well, you saved me, so thank you.” She hesitates. “And that’s the only reason you asked me? To save me from Tristan?”

Jess nods. “Yep. Only reason.”

“Not because you actually wanted to work with me or anything.”

“Nope.”

“Just making sure.”

“Be careful, Gilmore,” Jess says amusedly. “One might start to think that we’re friends.”

“And we wouldn’t want to give them the wrong impression, right?”

“Definitely not.”

Rory smiles despite herself. “Library after school, right?”

“It’s a plan.”

“I’ll see you, Jess.”

The corner of his mouth quirks up. “See you.”

Jess walks off to his next class, and Rory watches him leave for a moment before turning and going to her own class. There’s a funny feeling in her stomach, but it’s not unpleasant, not at all.

Maybe she actually has a friend at Chilton. 

Who would’ve thought it would be Jess?

**

Rory gets to the library first, so she scouts out a table and grabs a couple copies of _The Great Gatsby_ for them to work with. Jess shows up a few minutes later, wordlessly pulling up a chair and sitting down next to her. 

“Hi.”

“Hey.”

“How was the rest of your day?” She asks.

Jess snorts. “You’re very polite.”

“Yeah,” Rory says, frowning. “What about it?”

“No, no, I like it. It’s refreshing,” Jess assures her. “No one else asks; they’re rude as shit.”

Rory blinks a couple times, taken aback by his profanity. 

Jess laughs again. “Don’t tell me you don’t swear.”

“Not usually,” Rory says, somewhat defensively. “My mom doesn’t shy away from it, though. I’m not that sheltered.”

Jess shrugs. “Didn’t think you were. You’re a lot different than everyone else here.”

Rory frowns. “In a bad way?”

Jess shakes his head. “No. Everyone else is so...stuck up and selfish. It’s awful.”

“Why do you hate it here so much?” Rory asks after a pause. 

Jess frowns. “What?”

“Well, you say you hate everyone here, and you’re not trying very hard to do well at all...why do you hate Chilton so much?”

Jess hesitates. “I didn’t want to go here. But I didn’t have a choice. _That,”_ he adds, “was made _perfectly_ clear to me by my stepfather.”

“Oh.” Rory tries to get a read on him, to no avail. “But Chilton is a really good school, one of the best in the country. Why don’t you want the best education you can get?”

Jess begins folding one of his papers up, not looking at her. “I don’t need a bunch of stuck-up adults telling me what to think,” he says with distaste. “And I’m not going to go to college, so why does it matter?”

“No college?” Rory asks, taken aback by all this new information. 

“If the next word out of your mouth is ‘why,’ I’m going to have to revoke your question-asking permission,” Jess says, suddenly playful. “College might be a fit for you, but not for me.”

“But you still have to go to Chilton?”

“Yep,” Jess mutters. “My dear step-father pretends he’s doing it for my sake, but really, it’s all thanks to my mother.” He says that last part with such disgust that Rory is taken aback. “Mommy marries a rich guy, and I suddenly have no say in how I’ll live my life.”

“But why not take advantage of the opportunity?” Rory wonders, still surprised by what he’s said. “And why do you ha-”

“I’m not taking _anything_ from that man if I can help it.”

“You could do so much, though, if you just-”

“Rory,” he says gently, “I’m not gonna go to college, okay? Just drop it.”

“Okay.” Rory stares down at the table.

“I didn’t mean to make you feel bad,” Jess adds quickly. “Do you know where you want to go?”

“Harvard.”

“That’s ambitious.”

“It’s been my dream for...for forever,” Rory tells him. “Going to Chilton gets me one step closer, you know?”

Jess nods. “Makes sense.”

“Now, we need to start working,” Rory says, opening her backpack and pulling out her notebook. “We only have a _week,_ and we need to plan it out, and-”

“Give me a number.”

“What?” 

Jess holds up his paper, which he has folded up into a fortune teller. “Give me a number.”

Rory scowls and snatches it from his hands. “Focus.”  
“Ouch.” Jess watches as she crumples it up and drops it on the table. “I worked hard on that, I hope you know.”

“Yeah, I’m sure you were dying to tell me about how my life is going to turn out. Now, what characters do you think we should choose? Jess?”

Jess looks up from his notebook. “You like pizza?” He asks. “I know this great place not too far from here. We could go check it out.”

“Jess,” she hisses. “C’mon. We have two letters to write _each,_ and we need to decide on characters, and-”

“So, you don’t want pizza?”

“Jess!” She exclaims, frustrated, earning some glares from other students. “Stop fooling around, okay? We have one week to finish the project, and I refuse to put my Harvard career even more on the line because you don’t want to do the work. So suck it up, open the book, and pick some characters!”

Jess blinks in surprise at her outburst. “Okay, okay. I’m focusing.”

“Thank you,” Rory says stiffly, going back to her book.

She skims through the pages briefly before Jess speaks. 

“Tom and Daisy,” he says suddenly.  
Rory looks up from her book with a frown. “What?”

“We should do Tom and Daisy,” Jess says. “Tom is having an affair, and Daisy knows it, right? But she’s also looking for an escape in Gatsby, and he isn’t too happy about that, either. The whole book is about how the American Dream is some big illusion, and both Daisy and Tom are trying to hold onto that illusion in different ways. So, we have them try to explain their escapes to each other while resenting the other for their decisions.”

Rory blinks a couple times, processing his words. “That’s actually a really good idea, Jess,” she says, starting to smile.

Jess shrugs, but she can tell that he’s satisfied. “You sound surprised.”

“No, you’re really smart, Jess, you-”

“Rory,” he says, warning her.

“Right.” Rory opens her notebook. “Okay. Let’s start planning.”

She begins to scribble down some ideas, and when she looks up, Jess is looking at her with yet another expression that she doesn’t understand. “What?”

“Nothin’. We need to get this done, right? Do a good job so you can get into Harvard?”

“Tell me something I don’t know,” Rory says, half to herself.

“I like your hair.”

Rory lets out a half-laugh. “What?”

“I like your hair like that,” Jess says, gesturing. “It’s nice.”

“Oh. Thank you,” Rory says, somewhat bewildered - but she’s pretty sure she’s blushing, anyway. “It’s nothing fancy, really, it’s just...down. No headband or braids or anything.”

“I know. It looks good that way,” he replies. “Not that it looked bad any other way.” They look at each other for a moment before Jess clears his throat and breaks eye contact. “Okay. We’re planning.”

Rory’s gaze lingers for a moment, but she quickly looks away. She can’t read him, she hasn’t been able to this entire time she’s known him - which, admittedly, isn’t very long at all, but she’s usually pretty perceptive.

So why is he still such a mystery to her?

**

“Alright. I think we’ve done enough work for today,” Rory says, looking down at what they’ve written. “Outlining all four letters? We’ll probably be done early.”

Jess nods. “I guess we work pretty well together.”

“I guess we do.”

Jess shakes his head. “Who would’ve thought?” 

“Not me,” she says, teasing.

“Not in a million years.”

“How are you getting home?” Rory asks, beginning to put her belongings back in her bag.

“Driving,” Jess says, pulling a book out of his bag. “You?”

“The bus.”

Jess half-laughs, not looking up from his book. “My stepfather almost had a conniption when I said I would take the bus. So, I get a car.”

“You don’t sound very happy about that,” Rory notes.

Jess shrugs. “It’s a nice car. I can’t complain, right?”

“I don’t know. I’m not always comfortable with all of my grandparents’ fancy things. I’m just not part of that world, you know? I’m just glad that they’re paying my tuition.”

Jess glances up from his book. “Well, in that case, I fucking _hate_ the thing.”

Rory laughs. “Glad you could be honest about it.”

“Do you live outside of Hartford, then?” Jess asks. “If you have to take the bus.”

Rory nods. “Yeah. I live in Stars Hollow, which is this really small and wacky town that’s, like, forty minutes from here.”

There’s a strange look on Jess’ face for a moment, but it’s gone as soon as it came. “Don’t think I could ever live in a town. It sounds like hell.”

“It’s not that bad. Everyone knows each other, and-”

“Yeah, like I said, hell.”

Rory rolls her eyes. “Okay, who are you, Holden Caulfield?”

“I’ve never purported to be social.”

“I guess you haven’t. Does the _Cheers_ theme song give you hives?”

“Sometimes.”

“Then Stars Hollow wouldn’t be the place for you.” Rory glances down at his book; it’s worn and creased and he has it folded as he’s reading. She could never treat a book in a way that it would make it look like that - she’ll admit it, she’s a book snob. “What’re you reading?”

_“The Telltale Heart and other Writings.”_

“Oh, that’s a good one.”

“It’s fine. I’m still not a big poetry person, though. Although, _Howl_ is an exception.”

“You like to read?” Rory asks, somewhat surprised. 

Jess cocks his head to one side, reminding her a bit of Tristan - but Jess is better, so much better. “Yeah. Why? Do you?”

“I _love_ it,” Rory gushes. “There’s just something about reading and being transported to another place and experiencing a life that you would never otherwise know that I just...love.” There’s something in the way that Jess is looking at her that makes her heart skip a beat. “What?”

“Nothin’. You’re right.” Jess raises an eyebrow. “So, what’re you reading?”

_“Little Women.”_

“You don’t sound too happy about that,” Jess notes. “I would’ve assumed you’d like it.”

“I don’t know. It’s just…” She hesitates. “It’s so much _telling_ and no showing. Don’t just _say_ that Jo has a temper or that Amy is spoiled, actually _show_ it. You know?”

“I see what you mean.”

“Do you like it? I’d hate to think I’m trashing a book that might be your favorite or something.”

Jess snorts. “I wouldn’t go that far. It’s...okay. It’s just strange to me that Amy gets away with being spoiled and self-centered and fucking _burning Jo’s book,_ but Jo is always being told to check her temper. If I was writing a book, and someone burned it, you’d never hear from them again.”

“Maybe it’s a sibling thing,” Rory offers. “Jo _was_ based off of Louisa May Alcott herself, right?”

Jess grimaces. “I guess I’d have to affirm that from experience.”

“You have siblings?”

“A step-brother.”

“Oh. Who-”

“You should get going, right?” Jess asks, cutting her off. “Don’t want to miss your bus.”  
Rory nods; his evasiveness only increases her curiosity, but he obviously doesn’t want to talk about it, and she’s pushed him enough today already. “I probably should.”

“So, I’ll see you tomorrow, then?”

“Wait- let me give you my number. So we can keep in touch if we need to talk about the project,” she adds when he raises an eyebrow. 

“Alright.” Jess scribbles down his own number on a slip of paper. “Here. My cell.”

Rory writes down her own and exchanges it. “I added my home phone, too, just in case.”

“Thorough.”

Rory shoots him a look. “You have a problem with that?”

“No,” Jess says, shaking his head. “Have a good ride home, Rory.”

“Thank you.” She smiles. “I’ll see you.”

“See you.”

She purses her lips together to hold back a grin as she leaves the library. That familiar strange flutter in her stomach is back, she notices. What is it about him that’s making her feel this way?

But then she sees the bus and she thinks about Stars Hollow, and then she thinks about Dean, and her grin widens. A boy likes her. A boy actually _likes_ her. And she likes him. And she has a friend at school, now, too. 

She was right; she just had to stick it out, and everything would fall into place. 

**

“I don’t think Claudia’s planning to die a second time.”

“Mom, I couldn’t go if I wanted to.”

“Fine.”

Rory fidgets in her seat a bit, not enjoying the tension between her mother and her grandmother. There’s no relief, at least, not for her, because then Emily turns to Rory and asks, “So, Rory, how’s school going?” There’s a suggestive tone in her voice that Rory isn’t thrilled by. 

“It’s okay,” Rory says, taking a bite of her food. “My classes are good and I’m pretty much caught up with everything.”

“Oh, well, there’s no surprise there,” Emily says. “You’re the smartest girl I know.”

“And what am I, Albert Einstein’s dumb twin?” Lorelai interjects. “I’m sure Claudia would be offended as well.”

Emily rolls her eyes, but doesn’t dignify Lorelai’s objection with a response. “What else is going on at school, then?”

“Nothing, really. There’s a college fair in a week or two, so I’ll go to that.”

“Ah. Anything else?”

Lorelai frowns. “Mom, what are you trying to get at?”

“I was just wondering if Rory’s made any friends, or...met any boys,” Emily says, her voice heavy with implications. 

_“Mom,”_ Lorelai groans. “Rory doesn’t have to-”

“It’s fine,” Rory cuts in. “Really. I guess I’ve made a friend. Who is a boy,” she adds awkwardly. She hasn’t mentioned Dean to her grandmother yet, but she doesn’t want her to get the wrong impression about Jess. “Just a friend.”

“Oh, really? Who? You know, your grandfather and I know so many of the families there, maybe we’ll have met him.”

“His name is Jess,” Rory says hopefully - maybe her grandmother will know something about him. “Jess Mariano.”

“Mariano,” Emily says slowly, frowning. “No, I don’t think I’ve ever heard of the Mariano family.”

“But you expect me to know who Claudia is?” Lorelai demands.

“He said his mom remarried. Maybe Mariano is his mom’s name,” Rory suggests.

“Yes, maybe. I’m trying to think, but so many people have gotten remarried, it’s hard to say who it might be. It’s very interesting.”

 _“Fascinating,”_ Lorelai says. 

Emily shoots her a look. “Is everything a joke to you?”

“Only the funny stuff.”

As her mother and grandmother go back and forth, Rory takes another bite of her meal, lost in thought. So, her grandmother has never heard of the Marianos. That’s fine, it is, but she’s still no closer to knowing who Jess’ stepbrother is, or why he was so cagey about it when she tried to ask. So, really, she’s no closer to knowing any more about him than she was five minutes ago.

All it does is intrigue her even more. 

**

Cinnamon’s wake is nice - it’s always touching to see the town gathered together, even if it’s to mourn a cat. The night is good, even though Rory embarrasses herself in front of Dean (why is she so afraid to talk to him? She likes him, and he likes her. It really shouldn’t be this difficult). It’s good up until she sees Mr. Medina on her front porch. It’s fine, just a little weird, until Lorelai sits her down and tells her that she’s dating him.

Demanding why her mother didn’t tell her before, Rory feels an odd sense of déjà vu. There’s a few things that are being hidden from her lately, and a few people who are hiding things from her, but it’s good to know that she can take her mother off the list.

(As far as she knows. Part of Rory still wonders if maybe it’s a little more serious than Lorelai let on.)


	5. The Tell-Tale Heart and Other Writings

**Summary for the Chapter:**

> Rory's grandparents host a birthday party for her.

**Notes for the Chapter:**

> I hope you enjoy this one! I'm actually really happy with it - definitely one of my favorites yet.  
> NOTE: A small amount of dialogue is taken from 1x06 (Rory's Birthday Parties). You'll recognize when you see it - the rest is original.

Rory waits for the bus with Dean the Monday before her birthday. They’re not really anything, not yet, but he’s kind of just _there_ whenever she thinks of him, and she has to admit, it isn’t that bad. She tells him about the debacle with her parties, and when she’s done, he just shrugs and says, “Well, hey, it’s double the fun, right?”

Rory shakes her head. “It’ll probably just be a bunch of my grandparents friends who all met me when I was a baby, so that’ll be all we talk about.”

“No one you can invite from school?”

“Are you kidding? Everyone there hates me. Well, I have _one_ friend, but I don’t think he’s the party type.”

Dean frowns. “He?”

“Yeah, he,” Rory says, a little confused. “We worked on a project together last week, but he’s really not very social. I doubt he’d go, even if I asked.”

“Oh.” Dean picks at a loose thread at his shirt, still frowning.

“What is it?” 

“Nothing.” Dean looks up and smiles and Rory’s heart skips a beat as always. “I like your hair today.”

Rory blushes. “Really?”

“Yeah. Your hair looks better with headbands, I think.”

 _Note to self: wear more headbands._ “Thanks.” 

“No problem. I have to go to school now, but I’ll see you later?”

“Okay.”

Dean smiles again and as he walks away, Rory unconsciously goes to touch her headband. Maybe he has a point - she’s never hated the way she looks with one on. (And she likes the way he makes her feel when he compliments her, too.)

**

Rory’s taking her textbook out of her locker when out of the corner of her eye, she sees Tristan approaching her. She’s _really_ starting to dread this part of her day - whenever he corners her and she can’t do anything but stammer her way out of it. He makes her nervous, but not in a good way, not like when she’s around Dean and she says stupid things that just make him laugh. 

“Hey, Gilmore.”

Rory nearly jumps out of her skin. She whirls around, and when she sees Jess behind her, she lets out a relieved laugh.

“God, Jess, you scared the _hell_ out of me,” she says, laughing. 

Jess smiles and leans up against the locker beside hers, effectively blocking Tristan from approaching her. She holds back a grin when she sees Tristan glare at Jess and walk off in the other direction. “Sorry.”

“It’s okay.” Rory closes her locker and faces him. “Thanks for diverting Tristan, by the way. He won’t leave me alone.”

“I don’t know what you’re talking about,” Jess says innocently, but there’s a gleam in his eye that lets her know he’s not quite telling the truth. She notices his disheveled appearance once more, but tears her eyes away from his rolled up sleeves.

“I’m sure you don’t. What’s up?”

Jess reaches into his pocket and pulls out an envelope. “Just wanted to warn you that someone - I assume your grandparents - left _these_ in the lockers of everyone in our class.”

Rory snatches the envelope from him and opens it; her stomach drops when she begins to read it. 

_On the morning of October eighth at four-o-three in the morning, Emily and Richard Gilmore were blessed with a perfect baby granddaughter, Lorelai Leigh-_

Rory gapes down at it and then groans, thrusting it back at Jess. “Oh, _God.”_

Jess nods grimly. “Yep. I can say it was a prank, if you want.”

Rory shakes her head. “It’s fine. Thanks anyway, though.”

Jess shrugs. “No biggie.”

“As if I needed another reason to be the center of attention,” Rory grumbles, holding her textbook tighter against her chest. 

Jess looks at her sympathetically. “I’d tease you for it, but seems like everyone else is going to be doing plenty of that already.”

“I appreciate the restraint.” Rory falls back against her locker and closes her eyes. “Maybe if I wish really hard, it’ll turn out to all be a dream.”

“No ruby slippers for you, Dorothy,” Jess says, elbowing her lightly. “C’mon. I’ll walk you to your next class so you don’t have to face the whispers alone.”

Rory gives him a grateful look. “One second. I need to find the right poker face before I brave the crowd.”

“Understandable.”

“At least I have the party back at home to look forward to,” Rory says, half to herself.

“Two parties? Well, aren’t you the prodigal daughter.”

Rory shrugs half-heartedly. “Not really. My mom throws me a party at our house every year that people from all around town come to. Definitely the best part of my birthday every year.”

“Then look forward to that,” Jess says. The bell rings, letting them know that they have five minutes until class starts. “Come on. Let’s head to class.”

“I guess, but even that isn’t going to be on my actual birthday,” Rory complains, walking alongside him. “My grandmother insisted on hosting _her_ party on Friday night ‘cause that’s when we have our dinners, so. It has to be on Saturday night.”

“Well, then it’s two days of parties, right?”

“Hey, what happened to ‘ _I must insist on being a pessimist?’”_

“I can do that, too. It’s all going to suck and your parties will be a nightmare.”

“Okay, okay,” Rory laughs. “I get it.”

“Besides,” Jess continues, giving her a little nudge, “you deserve at least _one_ thing to look forward to, right?”

Rory thinks about Dean maybe showing up at her party at home and smiles a bit to herself. “Yeah, I guess so.”

“Glad we’re on the same page.”

“Wonder if anyone will actually show up,” she chortles. 

“Their parents might make them.”

Rory smiles. “So, what about you?”

“Oh, my birthday was in September. I’m not throwing any parties.”

She rolls her eyes. “That’s not what I meant and you know it.”

“And what did you mean, then?”

Rory huffs. “Are you going to come?”

Jess half-smiles and looks away. “Maybe. Why?”

“No reason,” Rory says, turning pink. “Just...would be nice if there was a friendly face there, you know?”

Jess chortles. “‘Jess Mariano’ and ‘friendly face’ aren’t words one would normally put together.”

“Well, no one else here likes me.”  
“Their loss,” Jess says, and Rory flushes even darker. “We’ll see, okay?”

“That’ll have to do.”

“It will. Here we are,” Jess says, leaning up against the doorframe of Mr. Medina’s classroom. “If we have to look at any more Dickens today, I’m going to tear my hair out.”

“No, don’t do that, you work so hard on it,” Rory says teasingly, reaching up to touch his gelled curls; he swats her hand away and gives her a look.

“Regardless, we’re doing Austen next, so that should be better.”

Rory frowns. “You like Jane Austen?”

“Jeez, what _is_ it with everyone assuming I don’t like Jane Austen?” Jess scoffs. “Of course I like Austen. Anyone with half a _brain_ likes Austen.”

“That’s true. I guess I just didn’t think you did - I mean, you’re always reading the Beats and Vonnegut and stuff. Not many people read that _and_ classic British literature.”

“Swift way to insult me, Gilmore,” Jess says, but he’s still sort of smiling like usual. 

“Oh, and you’re just _so_ sensitive.”

“You hurt my feelings on a regular basis - one would almost think it’s a hobby,” he teases.

Rory opens her mouth to quip back, but she’s cut off by Mr. Medina. “Hey, you two, class is about to start. Take a seat and we can get started with Dickens.” 

Jess grumbles, making Rory laugh. 

The two of them find their seats in the classroom. Once she’s set her things down, Rory glances back at Jess, but he’s already pulled out _England’s Dreaming,_ so she turns back around in her seat.

Okay, so, first, he’s the boy who’s kind of rude to her on her first day of school. Then he’s the boy trying to lift her spirits after a bad grade or an embarrassing incident. And then he’s this mysterious and cagey boy with dark, curly hair and a love for reading that rivals her own. He’s the boy who reads books about punk music in English class and reads Sandra Cisneros during lunch. But he’s also this boy who makes her feel strange, in a way she hasn’t really felt before, not around anyone, not even Dean. 

She feels something hit her back; turning around, she sees a paper airplane on the floor by her desk. She picks it up and unfolds it. In neat, focused handwriting that could only be Jess’, it says: _I’ll be there._

She smiles to herself for the rest of class.

**

“Why are you smiling?” Lane questions as the diner door closes behind Dean.

Rory tries to hold back her grin. “Oh, just thinking about pudding.”

Lane glances behind her to see Dean walking by the diner window. She turns back to face her friend, eyes wide. “Rory. Spill. Now.”

“There’s nothing to spill,” Rory laughs. “I just really like this pudding.”

“That’s B.S. and you know it,” Lane whispers. “Luke’s pudding is good, but it’s not _that_ good. Now, spill.”

Rory ducks her head, feeling her face heat up. “It’s not that big of a deal, really. Nothing’s actually _happened_ between us. We’re just...talking.”

“Talking?” Lane asks excitedly. “Talking about what?”

“Well, he said he likes my hair with headbands.”

“Aw,” Lane swoons. “Anything else?”

“Not really,” Rory shrugs, taking another bite. “Like I said, nothing’s really happened.”

Lane frowns, disappointed, but then her face lights up. “What about Jess, then?” 

Rory looks at her friend, confused. “What about Jess?” 

“What’s going on with him?”

“I guess we hang out between classes, but that’s pretty much it. Why?”

“I dunno. You just seem happy when you mention him.”  
“Well, he’s...nice to me, I guess.”

“I wish _I_ had two boys in my life,” Lane laments, looking at her pudding sadly. 

“Hey, Jess is not a...a boy in my life,” Rory objects. “He’s just a friend. And my _only_ friend at Chilton, might I add.”

“You talk about him a lot.”

Rory frowns. “I do?”

“Yeah.”

“Well, that’s just I don’t have anyone else to talk about from school,” Rory says defensively. “Besides, I don’t like Jess. I like _Dean.”_

Lane shrugs, looking unbothered. “Okay. I just thought that maybe something else was going on there.”

“Well, there’s not.”

“I believe you.” Lane grins. “So. Tell me more about Dean. You _know_ I live vicariously through you.”

**

The party is even _worse_ than she expected.

Rory doesn’t mind being the center of attention, not usually, but only when it’s in small quantities and when it’s preferably positive. But right now, she kind of just wants to hide away and cry. 

The party started an hour ago, and Jess isn’t even here yet, so there’s no one but her mom to be with, and she has a feeling her classmates would make fun of her for that. 

She’s about had it and is ready to cause a scene as she’s storming away from Paris when she sees who else but Tristan walk through the front door. 

“Oh, coming to greet me?” He asks in that pompous, good for nothing, _disgusting-_

She takes a deep breath. “Hello, Tristan,” Rory says curtly, trying to hold onto her composure and struggling.

He approaches her, hands in his pockets. “So, where’s my birthday kiss?”  
“It’s _my_ birthday.”

He steps closer. “So I’ll give _you_ a birthday kiss.”

“What is _wrong_ with you?” Rory demands angrily; she’s done playing nice with him.

Tristan claps his hands in front of him. “I gotta tell you something. I’m madly in love with you.”

“Well, good luck with that,” Rory says. She wants to walk away, but she’s reminded of how her grandmother would reprimand her, saying that _she’s_ the hostess, so she remains in place, praying for him to go away.

“I can’t eat. I can’t sleep. I wake up in the night calling out your name - Rory! Rory!”

“Would you shut _up,_ please?” Rory hisses. 

“Rory! Who’s your friend?” Rory turns her head to see her grandfather approach them. 

“I don’t know, but this is Tristan,” she says, her voice still full of disgust.

“Excuse me?”

“Tristan Dugray, sir,” Tristan says, holding out his hand for Richard to shake. Rory watches helplessly, hoping Tristan would just make a fool of himself and get himself kicked out.

Richard shakes his hand. “Dugray?” He asks, surprised. “Are you any relation to Janlen Dugray?”

Tristan nods. “That’s my grandfather, sir.”

“I’ve done business with Janlen for years. He’s a fine man.”

“He is.”

Richard looks over at Rory, looking pleased. “You have very good taste in friends. I approve.”

Rory wants to throw away all pretenses and yell _he’s not my friend!,_ but she misses her chance when one of her grandfather’s colleagues pulls him away, and she’s left standing there with Tristan. 

“He likes me,” Tristan says suggestively, leaning even closer. Rory catches a whiff of his cologne - great, now she hates a whole new scent. 

“He’s drunk.”

Tristan reaches out to take Rory’s arm. “Let’s take a walk.”

She shakes him off. “This is stupid! You don’t even like me. You just have this weird need to prove that I’ll go out with you.”

“Why are you fighting this? You’re gonna give in eventually,” Tristan says, stepping even closer, and Rory is reminded of a million feminist things her mom has told her, but she’s saved from having to say anything when there’s a knock on the front door.

The maid rushes to open it, and then Jess is walking through the threshold, looking uncomfortable as the maid takes his coat. 

He stands there, his collar buttoned unusually high and a disgruntled look on his face. “Jess,” she says in surprise, approaching him and ignoring Tristan. “I was starting to think you weren’t coming.”

He just shrugs. “Got held up. Sorry I’m late,” he mutters.

“It’s okay,” Rory says, blinking in confusion. 

Jess doesn’t say anything, his jaw set in a way she doesn’t recognize. 

“Tristan, go away,” Rory says, not even looking at him. 

“Fine. Good luck with _that,”_ the other boy snaps.

Once Rory makes sure that Tristan is out of earshot, she turns back to Jess, still bewildered. “Jess.”

“I’ve just had a bad afternoon, okay?” He says, agitated.

Rory snorts. “Apparently.”

Jess is still scowling and silent, so Rory grabs him by the wrist and drags him to her grandfather’s study, ignoring his objections. 

“Okay, what’s going on with you?” Rory demands once she’s closed the door. She’s never seen him like this before - dark and dangerous and truly _angry,_ eyes a little wild. It scares her, just a little.

“Nothing.”

“Bullshit,” she snaps, and Jess’ eyes widen, surprised by her swearing. “Something is going on with you, Jess. I don’t know what, but I know something’s up.”

Jess clenches his jaw and doesn’t make eye contact. “Rory, I’m fine.”

“Jess,” she says, almost pleading, “I know you’re not. I just want...I don’t…” She trails off, looking at him helplessly.

Something in him softens, because he just falls back into the armchair and sighs, the scowl gone from his expression. “Just...my step-dad's a jerk,” he says into his hand. “And these parties aren’t really my scene.” 

(She thinks about Tristan and wants to say _me, too,_ but she decides against it.)

Rory bites her lip and sits on the ottoman across from him. “You can talk about it, if you want to,” she offers, scratching at the back of her hand. “I don’t mind.”

Jess exhales slowly, closing his eyes. “It’s really not that big of a deal. He’s...not happy that I’m part of the family, and not afraid to tell me.”

“I’m sorry.”

“The last thing I want is pity,” Jess scoffs. “Look, he’s just not a nice guy. He isn’t exactly warm and fuzzy to my stepbrother, either, but he saves the yelling for me.”

“What did he say to you?” Rory asks, voice nearly a whisper.

Jess purses his lips together, and she realizes that his eyes are reflecting the lights in the room a little too well. “I am a burden,” Jess mumbles, “an inconvenience, and they were better off before me and my drunk of a mom became part of the family. He doesn’t know why he decided to use our newfound money for my tuition, but he regrets it. He-” Jess cuts himself off, and Rory’s sure that if he keeps going, he’ll break. (She doesn’t know what he means by “newfound money,” but she doesn’t ask; it’s not the right time.)

Rory stares down at her knees, her eyes filling with tears. “You don’t deserve that,” she mumbles, almost inaudible.

“Yeah, well…” Jess clears his throat. “The feelings are reciprocated, if that’s worth anything.”

“I’m-” She stops herself from apologizing and wipes her eyes. “I wish you didn’t have to deal with that.”

Jess stays silent, but he finally looks at her, gratitude clear in his expression.

“Thanks for coming despite it.”

“I told you I would, didn’t I?” He offers her the biggest smile he can muster, which isn’t much, but it makes her heart twinge all the same. 

“I’m glad you came. But you don’t have to stay, Jess, not if you don’t want to.”

Jess bites his lip. “You gonna be okay here?”

“Are you going to be okay at home?” She counters, worried.

Jess nods. “It’s just words. It doesn’t get worse than that.”

She doesn’t really know what to say to that, so she takes a deep breath, thinking about all the books she’s read where sons get hit and- “But you’re safe, right?”

“Yeah.”

“Okay.” She glances over at him. “Maybe you can call your mom to pick you up.”

That’s the wrong thing to say, apparently, and she’s instantly reminded of his _drunk of a mom_ as his guard goes right back up. “I drove,” is all he says.

She nods, face burning in embarrassment. “Okay.”

He looks like he’s suffocating, she thinks, under the pressure of his stepfather and their school and this _house._ She reaches over and unbuttons the top two buttons of his collar, his breath hitching when her fingers brush against his neck.

She pulls away, hoping that what she just did was okay; he offers her a gentle look to let her know that it was. “Better,” he says, voice a little hoarse. She smiles. 

The two of them stand and exit the study, Rory leading the way. “Goodnight, Jess,” she says, handing him his coat from the closet.

He smiles a sad smile that makes her heart lurch. “Happy birthday, Rory.”

The door shuts closed behind him. 

**

When she and her mother are putting on their coats to leave, Rory feels something in her pocket. She reaches in and pulls out a book. When she sees the title, she smiles.

“What is it?” Lorelai asks, looking down to see what her daughter is holding.

 _“The Tell-Tale Heart and Other Writings,”_ she says. “It’s Edgar Allen Poe.”

“Who’s it from?”

Rory notices the wear and tear, and opening it, she immediately recognizes the writing covering the page. “It’s from Jess.” _He writes in the margins._

“Jess?” Lorelai wonders, frowning. “I didn’t think he came.”

“He was here for a little while,” Rory explains, closing the car door. “I guess he must’ve slipped it into my coat pocket when I was getting his coat for him.”

“It’s kind of a beat up book,” Lorelai notes. She starts the car and glances over at Rory questioningly.

Rory smiles to herself. “It’s his copy.”

“Oh?”

“Yeah. He read it after we worked on our project a couple weeks ago.”

“Why’d he give you his copy?”

“I don’t know.” Rory runs her finger down the binding. “But I like it.”  
“I’m glad,” Lorelai says with a smile. “Now, let’s leave this hell of a night behind, huh?”

**

When they get home, Rory crashes immediately, barely having any time to get in her pajamas. She’s _so_ tired, so even though she wants to read through the book Jess gave her, she falls asleep before she can even turn off her lamp.

**

The next night, Dean’s bracelet on her wrist, she settles onto her bed, opens Jess’ book, and begins to read. 

And read, and read, and read. 

**Notes for the Chapter:**

> How we feeling?


	6. The Scarlet Letter

**Summary for the Chapter:**

> A rumor is spread.

**Notes for the Chapter:**

> Hey, everyone! I know things are pretty shitty lately, but I'm really thankful for all of you that continue to read and support this fic. I won't get overly sentimental here, but I love seeing all of your comments and hearing all of your theories. I hope this fic is something you can look forward to.  
> Love you guys!

Rory doesn’t feel any  _ different, _ not really, now that she’s been kissed - she doesn’t even know if she’s supposed to, anyway; no, she’s still Rory, still awkward around Dean, but still head over heels for him. And isn’t that what counts?

On the ride to school the next Monday, Rory tries to swallow her excitement (she can’t wait to see Jess, and tell him about what happened) and takes out  _ The Tell-Tale Heart and Other Writings. _ She’s read it a little every day since she found it in her coat pocket; she can already tell which part is his favorite -  _ Eleonora - _ because that’s where it opens to naturally.

(She looks at the lines he has underlined and reads his notes, hoping to find some way to understand him better. While that doesn’t really help, she can still see why he likes it, though, with  _ they who dream by day are cognizant of many things which escape those who dream only by night...in their gray visions they obtain glimpses of eternity, and thrill, in waking, to find that they have been upon the verge of the great secret...) _

**

When Rory arrives at Chilton, a familiar face is leaning up against the wall, waiting for her. She grins to herself and walks towards him, taking her time.

Jess glances up from his book and smiles when he sees her. “Hey, Gilmore.”

“Hey, Jess,” she says cheerfully. “How was your weekend?”

Jess raises an eyebrow. “What’re you so happy about? Did something happen?”

“Is it that obvious?”

He grunts amusedly. “You look like you won the lottery or something. What happened?”

Rory bites her lip to hold back a grin as they enter the school. “Promise you won’t tell anyone?”

Jess rolls his eyes. “And who would I tell?”

“Okay, okay,” Rory laughs, nudging him in the side. “Something...something happened this weekend.”

“Figured as much.”

Rory ducks her head, trying to contain herself.  (She’d already excitedly gushed about it to Lane over the phone, and she could’ve called Jess and avoided the awkward interaction part, but she wanted to tell him in person. (They’re friends, she  _ thinks,  _ and while she wants to share this with him, wasn’t it too soon to call?))

“Well, don’t keep me in suspense.”

Rory pulls him aside up against some lockers. Her eyes dart around before she leans in and whispers, “I had my first kiss.” She feels her face heat up a bit.

Jess blinks for a moment, seemingly processing what she’s told him. He doesn’t say anything, so she continues, saying, “There’s this boy back home named Dean. We’ve been kind of...well, there’s been something there for a while. He actually kissed me, and then my mom invited him over for a movie night. It was really awkward, but...it was fun,” she admits, a flush creeping up her face. 

There’s a strange expression on Jess’ face that Rory cannot decipher, but she’s sure that if she keeps talking, she’ll just end up rambling, so she waits. After a moment, Jess gives her a smile. “Congrats, Rory.”

“Thanks,” she says, sure she’s blushing. “I just...wanted to tell you, I guess.”

Jess swallows and nudges her. “Tell me more about it, huh?”

“Like what?”

“Was it good? Does he know what he’s doing? Or was it the kind that made you run away?”   
“Well, I ran, but not because it was bad.”

Jess laughs. “Of course you did. What happened?”

She sticks her tongue out at him. “You’re mean.”

“Yes, that is me.”

Rory smiles. “He told me to close my eyes and then he kissed me. I freaked out, so I said thank you and ran. I accidentally shoplifted, too.”

Jess snorts. “Seriously?”

“Yeah. Cornstarch.”

Jess shakes his head. “Well, at least you were polite.”   
“I committed a crime!”

“But don’t we all do foolish things for love?”

“Oh, shut up.”

**

She sits with Jess at lunch for the first time today. They both pull out their books -  _ Persuasion  _ for Jess and  _ The Tell-Tale Heart and Other Writings  _ for Rory, of course - but after a little while of reading, Rory sets her book down. She’s been up to her neck with questions these days, and she’s still got a little bit of nerve left over. 

“Jess?”

“Hm?”

“So, I told you about my first kiss.”

His expression hardens. “That is a fact.”

“I’ve told you a lot of things about myself.”

“Yeah…”

“But I still don’t know anything about you.”

Jess sets his book face down on the table, looking straight ahead. “You know a little. I filled you in about the kind, loving person that my stepfather is. Oh, and that my mother is an alcoholic. That didn’t fill the quota?”

Rory blushes. “I just...want to know more about you, I guess.”

Jess sighs. “There’s not much to tell, Rory.”

“Tell me about your first kiss, at least,” Rory offers. “That’s low stakes, right? Unless you haven’t had it…” She adds when he doesn’t reply.

Jess snorts. “I have.”

“Then tell me!”

He glances over at her warily. “Why do you want to know so bad?”

“I - I don’t know. I mean, we’re friends...right?”

He smiles - barely, but it’s there. “We are.”

“Then you have to tell me,” Rory says matter-of-factly. “Friends tell each other things.”

“Hold on, I didn’t get the slumber party invite.”

Rory rolls her eyes. “Are you incapable of giving a straight answer?”

“Juliet D’Angelo.”

Rory blinks in confusion. “What?”

Jess looks at her amusedly. “My first kiss was with Juliet D’Angelo.”

“Oh.”

“What? You jealous?” 

“No, I’m not.”

“Didn’t think so.” Jess takes a bite of his food, chews, swallows. “I was...thirteen. It was under the fire escape of the apartment building I was living in then in New York.”

“Wait - you’re from New York?” Rory clarifies. The way he gives her information can make her head spin - nothing, and then rapidfire facts that she tries to hold onto like treasures.

Jess nods. “Lived there up until last year when my mother married my stepfather.”

“Do you miss it there?”

A wistful expression passes across Jess’ face. “Not really,” he says with a shrug, but Rory doesn’t buy it. 

Regardless, she smiles. “So, Juliet.”

“What about her?”

“Well, did you date her or something?”

Jess snorts. “I forget how idealistic you are sometimes.”

Rory makes a face at him. “And what’s that supposed to mean?”

“Nothin’.” Jess takes another bite. “We didn’t date. I think that was the only time we ever kissed.”

“Oh.” Rory picks at her food a bit, processing what he’s told her. “Have you dated anyone?”

“And what’s the definition of ‘dated?’”

“I don’t know. To go out with someone repeatedly? While having feelings for them?”

“The two aren’t exclusive?”

“Hey, remember that thing about you giving a straight answer?”   
“No, I haven’t dated anyone,” Jess says, catching her off guard. “I’ve...been with girls. But while having feelings for them? No.”   
Rory frowns. That doesn’t really fit the picture of him she’d had in her mind. He’s  _ Jess -  _ how has he never been in love before? Has no one ever fallen for him? It doesn’t make sense. 

She must appear to be lost in thought, because Jess starts laughing. She looks over at him, confused. “What?”

He shakes his head. “Nothing. Just...the look on your face. You looked almost disappointed.”

“Why would I be disappointed?”

Jess shrugs. “Your guess is as good as mine.”

He’s still looking at her, amused, so she swats at him. “It’s not funny.”

“It is, a little.”

“Can I join you two?”

She looks up to see Tristan, standing over their table with a smirk. Jess’ jaw clenches tighter than she’s ever seen it. “No.”

Tristan ignores Jess, taking a seat across from the two. “So, are you two a thing now or something?” He asks casually, seemingly unbothered.

“Excuse me?” Rory demands. 

“You’re hanging out a lot these days. It’d be cute if it wasn’t so nauseating.”

“Would you go away?”

“Well, are you?”

“No, of course not. Are you okay? Do you have a fever or something?”

“I was just curious,” Tristan replies innocently. “‘Cause that’s not what I’ve been hearing.”

“Oh, shut up,” Rory snaps. 

“Anything to add, Jess?” Tristan asks. “Is she telling the truth? Mary still...Mary, or do I have to change her nickname?”

“What exactly are you on about, Tristan?” Jess asks shortly. 

“I think you can guess. Mary’s pretty smart.”

“We’re not together. This whole conversation is idiotic.” 

“I guess I was wrong.” Tristan looks between the two of them before focusing back on Jess. “I worry about you, you know, Jess. So closed off and grouchy...one would start to worry that you’re going down the same path as your dear mother.”

“What do you know about his mother?” Rory demands angrily. “None of it is  _ any _ of your business.”   
Tristan grins, evidently enjoying this. “Who doesn’t know about his mother? Everyone in our class knows that she’s a  _ drunk.” _

Rory glances over at Jess, giving him a worried look. There’s a scary expression on his face as he glowers at Tristan. “You don’t know anything about my mother.”

“If you say so. Just stay away from the alcohol, okay?” Tristan says, fake concern in his voice. 

“What the hell is your problem with him?” Rory suddenly exclaims. “What the hell did Jess ever do to you, Tristan? Huh? What gives you the right to treat him like dirt all the time? ‘Cause as far as I can tell, nothing excuses that!”

“Rory,” Jess says in a warning tone. 

Tristan stares at her in astonishment before an impish smile spreads across his face. He leans a little forward, edging in on her space. “There are certain types of people who belong here, you know? And Jess just...isn’t one of them.”

“And why is that, huh?” Rory demands. 

“Rory,” Jess says through gritted teeth. “Please.”

“What? You tired of stealing from other people, Mariano?” Tristan spits out. “You don’t belong here. You never did. And you don’t belong with  _ anyone _ here.”

Jess’ hands are clenched into fists so tight that his knuckles are white. “Tristan,” he says evenly, only the slightest quiver in his voice, “leave. Before I do something that we’ll both regret.”

Rory marvels at Jess’ composure as he stares Tristan down - but looks down and notices that his hands are shaking. Tristan glares at Jess one more time before standing up. 

“Say hi to your dear old mother when you get home. Oh, and be safe, you two,” he sneers before storming off. 

Rory looks back at Jess, who she knows is about two seconds away from breaking. “Jess-” She starts, but he cuts her off.

“Don’t say anything,” he snaps. Then, in a gentler voice, he adds, “please.” 

(It’s barely a whisper.)

Rory nods and stares down at her food. Under the table, she reaches over and squeezes his hand.

He squeezes back.

**

Rory thanks her math teacher and leaves the classroom, heading towards her next class. Stepping into the hallway, immediately, she knows something is off.

Now, she’s not new to people looking at her and whispering, but today, it’s worse than usual, so much worse. She hasn’t seen Jess since lunch, and she starts to worry. They don’t have all their classes together, but they usually meet up in the hallway. So is this about him? And what does it have to do with her? 

“So, no longer Mary, huh?” A boy sneers as she walks by, earning some snickers from people close by. Rory turns bright red and stares down at her shoes. 

“Is it true that she’s...” 

“Yeah, that’s her. It happened at her own birthday party, too.”

“Guess she  _ really  _ didn’t like that nickname.”

“I’m not surprised. It’s always the quiet ones, isn’t it?”

Rory stops at her locker to put her math textbook away, wanting to cry. She doesn’t understand why this is happening - she didn’t do  _ anything. _

Closing her locker, Rory feels a tap on her shoulder. She whirls around, and to her surprise, it’s Paris. 

“I don’t have the patience for this right now, okay?” Rory snaps,her voice cracking. “Just leave me alone.”

“Hormones, huh?” Paris asks condescendingly. She  _ tsks.  _ “It’s always the ones you least expect.”

“What are you talking about?”   
Paris’ brows draw together in thought. “I’m talking about how you had sex with Jess Mariano at your birthday party. What, do you have memory loss or something?”

Rory gapes at Paris, her blood going cold. “What?”

“It’s true, right?” Paris asks. “I heard you’re pregnant, too. I sort of feel bad for you, you know. Following in your mother’s footsteps like that...it’s kind of pathetic.”

“I don’t know what you heard, but that is  _ not  _ true,” Rory hisses. “And I’d appreciate it if you didn’t tell other people it was, okay?”

Paris frowns. “So, you didn’t sleep with Mariano?”

“No! Why is everyone saying that I did?”

“Everyone saw you go into that office with him at your party. I guess someone heard...something, and decided to tell the masses.”

“Well, no one heard anything, because it didn’t happen!” Rory exclaims, wiping at her eyes.

“Don’t get all weepy on me,” Paris says, taking a step back. “I guess I believe you. Sort of. But if it isn’t true...then  _ someone _ had to have said something.”

“How do I know it wasn’t you?” Rory snaps. “You hate me. I’m sure you’d love to humiliate me like this.”

“Hey, I may not find this completely unamusing, but it wasn’t me. I don’t make things up and spread them. If I start a rumor, it’s based on cold, hard facts.”

“Then who was it?”

Paris shrugs. “Hey, I don’t know, okay? Maybe it was Mariano. Guys love doing that for street cred.”

“Jess wouldn’t do that,” Rory retorts. 

“How do you know that? No one knows anything about him except that his mom is an alcoholic. Maybe he just wanted something good out there about him.”   
“He wouldn’t,” Rory repeats, but she’s starting to doubt herself. Paris is right - she doesn’t really know anything about him. Is it possible that he would betray her like this?

No. No, it’s not. Her fleeting doubt is replaced with absolute certainty. Jess would never, but she has a feeling someone else she knows would.

“It’s not Jess,” she says firmly. “But I think I know who it might have been.”

**

After the last period, Rory packs up her stuff and puts on her coat as quickly as she can, hoping to leave as soon as she can, but the murmuring and pointed stares just make her want to sit down and cry.

As she’s walking down the hall, head down, Jess catches up with her. “Rory.”

“I’m going home, Jess. I’ll see you tomorrow.”

“Rory, please, can we-”

Rory tries to speed up, but Jess grabs hold of her arm. His grip is loose, but still firm. She stops walking and slowly turns to face him, face burning red. “What do you want, Jess?”

“I wanted to make sure you were okay.”

Rory’s heart lurches at his words; she almost lets out a sob. “Do I look okay?”

Jess bites his lip. A kid she doesn’t recognize walks by and claps Jess on the back, making Jess wince. “Good score, man.”

“Shut up, Xavier,” Jess mutters, but the boy is already out of earshot.

_ “Everyone _ thinks we...we did  _ it,  _ Jess,” Rory says, her lower lip quivering. “Everyone.”

“I know.” Jess glances behind him, and sure enough, everyone is staring at the two of them and whispering. “Maybe it’ll blow over soon.”

Rory shakes her head. “It won’t. They’re - they’re saying I’m…” 

“You’re what?” Jess demands, somewhat harshly.

Rory swallows. “Pregnant,” she mumbles, not looking at him.

“And they won’t figure out that you’re not when you don’t have a baby?”

“They’ll find a way to keep it going. They all hate me so much,” Rory chokes out, wiping at her eyes, humiliated. 

Jess curses under his breath. “Screw this,” he says. He turns around to face everyone, a determined look on his face that Rory has never seen before. “Hey, all of you, shut the  _ fuck  _ up. I don’t care what you’ve heard, but Rory and I did  _ not _ have sex, not at the party or anywhere else, and she is definitely  _ not _ pregnant. If I hear  _ anyone _ talking about this again, I’ll fucking snap you in two.” 

Rory blinks at him in awe. The hallway is silent for a moment before everyone goes back to their conversations. She listens, but she doesn’t hear her name. 

“Jess, I-” She starts.

“Mr. Mariano, a moment, please?” 

Rory looks over to see Headmaster Charleston standing over them, a stern expression on his face.

Rory looks at Jess helplessly, but he doesn’t make eye contact. Without a word, he walks away with Charleston.

Rory stands there, watching his figure recede down the hall. When she finally turns to leave, she spots Tristan. Before she can lose her nerve, she storms over towards him and grabs him by the arm.

“I know it was you,” she says. When he raises an eyebrow and starts to talk, she cuts him off. “No, you don’t get to say anything. I know you spread that rumor about me and Jess, and I just want you to know, I don’t care. You can say anything about me, but it won’t make me not be friends with Jess, and it won’t make me want to be with you, either. Good _ bye.” _

And with that, she storms off.

**

Rory waits in the courtyard, sitting on a bench as she watches people leave. Finally, she sees Jess, and catches his eye. He makes his way towards her and sits down beside her.

“What did Charleston want?” She asks quietly.

Jess lets out a deep sigh. “I have detention.”

_ “What?” _

He nods. “Apparently, the use of profanity and violent threats are grounds for suspension, but he’ll let me off with a warning and detention for the rest of the week, starting tomorrow.”

“That’s so not fair. And Tristan gets no punishment at all?”

Jess shakes his head. “It’s not like they can trace it back to him, or that they’ll try. Besides, even if they did, it’s not like he’ll admit it.”

“But it was him, right?”

“I think that’s a safe bet.”   
Rory bites her lip, feeling the tears press against the back of her eyes. “I’m sorry about all of this.”

“It wasn’t your fault.”

“I-”

“Rory,” he says, so gentle it breaks her. “It wasn’t your fault.”

Rory squeezes her eyes shut. She opens her mouth, but she can’t do anything but start to cry.

Jess sits there awkwardly for a moment before tentatively wrapping an arm around her. She leans into him, sobs wracking her body, and he stiffens, but eventually he relaxes and holds her closer.

“I don’t - I can’t-” She stammers, but Jess just shakes his head. 

“It’s okay,” he says and holds her. He rests his chin on her head, his hand stroking her back. 

They stay like that for five minutes. 

**Notes for the Chapter:**

> Hope you guys enjoyed! Hope I can get the next one done in time, but my birthday is tomorrow, so we'll see.


	7. War and Peace

**Summary for the Chapter:**

> Chilton hosts its Winter Formal, and Rory finds herself in the center of a fight between two boys.

**Notes for the Chapter:**

> Hey! Hope everyone is doing well this week. Things are getting pretty scary, so I hope all of you are staying at home if you can. Here's another chapter - I hope it helps you take your mind off of everything, even if just for a little.  
> DISCLAIMER: There is some recognizable dialogue from 1x09 (Rory's Dance). As you know, I hate using scenes from the show, but like before, it was what was best for the flow.

Kissing Dean is nice. It’s new, and a little scary, but it’s also safe, which Rory likes. It doesn’t go too far, but it’s not bad. She likes it here, right in the middle.

A downside to kissing Dean, though, is that she’s not paying enough attention to Lane. She feels bad, and she feels like they’re on the edge of some huge fallout, but then Dean just kisses her again and she forgets all about it. 

When she gets to school, Jess is waiting for her. He’s been doing that every day since the rumor spread, and she has to admit, she likes it a lot. It’s nice to have someone who waits for her. Waiting. That’s what she’d like - for everyone to have just a little patience. She doesn’t even know if Dean is her boyfriend or not. So when Dean kisses her, she’s convinced that Lane needs to be a little patient while she figures all of this out.

But then, she gets to school, away from Dean, and away from Lane - and the guilt starts to eat at her. So when she walks up to Jess, looking sullen, he frowns. “Jeez, did your fish die or something?”

“You’re hilarious.”

“Seriously. You look upset. What’s wrong?”

Rory exhales slowly. “Walk with me.”

They walk down the hallway together towards Rory’s locker. Her eyes are fixated on the way his hands play with the strap of his messenger bag. “I’m a bad friend,” she says miserably.

Jess stares at her, confused. “What do you mean?”

“I’m totally neglecting Lane,” Rory laments. “I  _ know _ I am, but it’s just - it’s Dean,” she says helplessly. “He’ll kiss me and I’ll just totally forget about her. I’m a horrible person.”

“You’re not a bad person, Gilmore.”

“I know. I said  _ horrible.” _

Jess laughs. “You’re not dramatic at all.”

If it were anyone from Stars Hollow, she would be reminded that she’s  _ Rory,  _ and she can do no wrong. She’s just really into a guy. But then she looks at Jess, and it’s different; she knows that that’s not what he’s thinking. “Just say it.”

“What?”

“Whatever you’re thinking. Say it.”

Jess hesitates. “It’s not okay that you’re not paying attention to your friend, but you’re aware of it. So you have to find a way to fix it. You’re not a bad person, but it is something you need to do something about.”

Rory bites her lip and nods. “You’re right. You’re totally right. I just...I don’t want to hurt Dean, either.”   
“He shouldn’t get offended if you want to spend some time apart. I get that it’s the honeymoon phase and all, but Lane was there first, right?”

“Yeah.”

“So, make the change. Be there for Lane. Make out with him a little less.”

Rory flushes a bit, but she nods again. “You’re right.”

“Well, I usually am.”

She elbows him in the side. “Don’t be pompous. It doesn’t become you.”

“So, are you dating Dean now? Is he your boyfriend?” Jess asks suddenly, ever the slightest change in his tone.

“Honestly? I don’t know,” Rory admits. “We’re...something. Something exclusive. But we haven’t talked about it.”

Jess nods. “Cool.”

Rory raises her eyebrows. “Got something on your mind?”

Jess shrugs. “No. I just…”

“What?”

“Tell me about him. What does he like? What do you two talk about?”

“Well, I haven’t known him for  _ that _ long,” Rory says, a little defensively. “But he likes Nick Drake. And we talk about movies. And books, sometimes, but he hasn’t read as much as me. He keeps saying I need to read Hunter Thompson.”

Jess grunts. “Well, he’s got some taste, I’ll give him that.  _ Fear and Loathing  _ is pretty good.”

“Which one? In Las Vegas or on the Campaign Trail?”

“Both.”

“Oh.” Rory tucks some hair behind her ear. She didn’t wear a headband today, she realizes. “I had to  _ beg _ him to read Jane Austen, though. I think he liked it, even if he wouldn’t admit it.”

Jess scoffs. “What? Does it threaten his masculinity or something?”

Rory pulls away a bit and frowns at him. “What’s up with you?”

Jess shakes his head. “Just tired. Continue. What Austen did you have him read?”

She suspects he’s not being truthful, but for the sake of telling him more about Dean, she shakes it off.  _ “Pride and Prejudice.” _

“Could be beginner’s luck. Give him  _ Persuasion  _ or  _ Mansfield Park  _ \- those are the real tests to see if he actually likes Austen.”

“You’re so cynical.”

“Thank you.”

“But other than that,” Rory continues, “I don’t know. He’s from Chicago.”

“Cubs or Sox?”

“I haven’t asked.”

“Well, do so and report back,” Jess says.

“What do you care? I bet you’re a Yankees fan, anyway.”

Jess scoffs. “That was uncalled for.”

“What? Do you not like the Yankees?”

Jess rolls his eyes. “No one in their right mind should be a Yankees fan.”

“Why not?”

“Have you seen that episode of  _ Cheers _ where that Yankees fan comes in and harasses Sam?”

“I think so.”

“Let’s just say they didn’t make that up for views.”

“Okay, okay, I get it,” Rory says, rolling her eyes. “So you’re a Mets fan, then?”

Jess’ expression hardens. “My mother more so. But I think she just liked being able to gamble and drink booze.”

Rory opens her mouth to ask more questions, but the look on his face scares her a little too much. So, she changes the subject. “Is there anything else I should tell Dean to read?”

“Ask him if he really read  _ Fear and Loathing in Las Vegas  _ or if he just watched the movie,” Jess suggests. Rory hits him in the chest.

“Ever think of moving to Chicago yourself? I’m sure you’d make it big.”

**

The news about the dance spreads pretty quickly, but Rory doesn’t really even think about it until her grandmother brings it up. She didn’t want to go before, and she doesn’t want to go now, but surprisingly, it seems to be one thing her mother and grandmother actually agree on.

(Not that her mom will admit it, though. She stands firm on her belief that it’s Rory’s decision, but Rory knows that she thinks she should go.)

She has to admit, though, she’s kind of getting excited. She never went to any dances at Stars Hollow High - she only ever cared about the prom, and that’s  _ eons _ from now - but her mom is making her a dress and Dean agreed to go so maybe, it won’t be too bad.

**

Rory gets her tickets on Monday. The line is pretty long, but she gets there early enough so she doesn’t have to wait super long.

The phrase  _ and then Tristan _ appears is getting pretty old to her, but she steels herself as she sees him approach. She could hear him flirting with Paris, which made her skin crawl, but she keeps her tongue to herself.

“And she’s reading again. How novel,” Tristan drawls, coming to a stop at her side.

Rory glares at him. “Goodbye, Tristan.”

“Well, did you get the novel thing, because-”

“I said  _ goodbye,”  _ Rory interrupts. She goes back to her book again, but it’s a lost cause.

“What are you doing here?”

“I like lines,” she says flatly. 

“The  _ guy’s  _ supposed to buy the tickets,” Tristan says, leaning in.

Rory fights the urge to push him away. “Really? Does Susan Faludi know about this?” She asks, knowing for a fact that he won’t know who that is.

Tristan simply smirks, pushing right past it. “Unless there  _ is  _ no guy.”

“No, there’s a guy.” 

“A  _ cheap  _ guy.”

Rory wants to shoot back that maybe not everyone is as wealthy as him, but she holds her tongue for the sake of making this conversation as short as possible. “Well, what can I say? I like ‘em cheap. Sloppy, too - bald spot, beer gut, the pants that kinda slip down in the back, giving you that good plumber shot,” she says with a phony smile. “That sends me through the roof.”

“So, who is he?” Tristan asks, ignoring her attempts to just get him to  _ stop. _

Rory takes a deep breath, trying to keep herself calm and collected. “How many languages can you say ‘none of your business’ in?”

The line moves up, and Tristan follows. “Does he go to this school?”

“No, he doesn’t.”

“Uh-huh,” Tristan says, and she can tell he could care less about her having a date. “Well, look, okay, I’ll confess something to you. I don’t have a date.”

Rory looks up from her book and gives him a cold look. “Well, I hear Squeaky Fromme’s up for parole soon. She’d keep a good thought.”

Tristan smirks. “Well, I actually thought  _ you’d  _ like to go with me.”

_ Is he kidding?  _ “You did not.”

“I did, too.”

“You did not, because you are not  _ stupid.” _

“Why, thank you.”

“Slimy and weaselly, yes - but stupid, no. You’d have to be stupid to think that, given our history, I’d ever, barring a piano or a safe falling on my head, wanna go anywhere with you. Ever.” 

Tristan gives her a stone cold look. Finally, she’s driven him away. She’d almost feel bad if it wasn’t  _ Tristan. _

“Okay, fine. I’ll take Cissy.”

(If he’s trying to make her jealous, it’s almost laughable.)

“I’ll send her a condolence card,” Rory says, not looking up from her book. 

“Yeah, well, at least she won’t be buying her own ticket,” Tristan spits. Rory gives him a look before he walks off and she continues reading. He’s getting more and more aggressive, she notes, in his attempts to pursue her. What the hell is he trying to prove?

Finally, it’s her turn to buy tickets. Her eyes widen in exasperation when she sees who is behind the table. “Two, please.”

Paris snatches the money from her. “Idiot.”

“Excuse me?”

“He was totally nice to you, and you were a jerk,” Paris spits out.

“You like Tristan so much,  _ you _ go out with him,” Rory retorts. Since when is the way Tristan treats her considered  _ nice? _

Paris just hands her the tickets. “I don’t have change,” she says curtly, not making eye contact.

“Pay me later.”

“What am I, your versateller? Wait for change. I need change! Now!” She yells at the poor boy sitting next to her that Rory recognizes from her literature class. Paris turns back to Rory just in time to catch Rory’s eye roll. “There’s no way you’re going with someone better than Tristan.”

Rory gives her a flat look. “Whatever.”

“You probably don’t even  _ have  _ a date. You’re probably gonna come down with some rare form of flu that only hits losers on dance night. Or better yet, you’ll probably pay Mariano to go with you. Everyone thought you did it with him for a hot second there, so might as well, right?”

“You know what? I don’t want my change. Money makes people shallow,” Rory retorts calmly. She turns away and tries to hold back a grin as she hears Paris call after her, “I’ve got your change! Hey. Hey!”

Rory can’t hold back a grin as she turns the corner. 

“What’s so funny?”

She looks up to see Jess. “Oh, nothing. I  _ finally  _ got one in at Paris.”

Jess smiles amusedly. “Oh, yeah? What’d you say to her? Something about melting a witch?”

“She was giving me a hard time for turning away Tristan and ragging on me about how she has to give me my change, so I just told her that money makes people shallow and walked away.”

Jess lets out a laugh. “How red did she get?”

“It was more like fifty shades of purple.”

“Either way.”

“It felt good.”

“I bet it did.” Jess shakes his head. “So, what was Tristan doing?”

Rory groans, earning another laugh from Jess. “Somehow, he’s still under the impression that I really do want to go out with him, even though I have vehemently denied him multiple times.”

Jess rolls his eyes. “Of course he does. I have never met anyone so full of themselves as he is.”

“He was saying something about how he was thinking I should go with him, and how the guy should be buying the tickets.”

“Does Susan Faludi know about this?”

“That’s what I said! But I don’t think he got it.”

Jess snorts. “I’d be very surprised if he knew who she was.”

“I  _ told  _ him I had a date, but he didn’t care. He just went right on and asked me to go with him. Can you believe it?”

“So, you’re going with Dean, then?”

Rory smiles to herself. “Yeah, I asked him yesterday.”

Jess nods. “And how much convincing did it take to get him to go?”

“What’s that supposed to mean?”

Jess shrugs. “From what you’ve told me about him, he doesn’t seem like the dance type.”

“Oh, and you are?”

Jess’ expression softens just a little and he raises an eyebrow, inviting her to answer his question.

“Yes, I had to do a little arm twisting, but he agreed to go. I doubt he’ll wear a tie, though.”

“Will he be wearing pants?”

“No. I’m into flashers, remember?”

“Right, my bad.”

Rory nudges Jess. “What about you? Are you going?”

Jess scoffs. “That’s almost hilarious.”

“So, I take it you’re not going.”

“It’s a cold day in hell when I go to one of those things.”

“Come on!” Rory exclaims. “Look, if I have to go, you might as well, too.”

“Don’t you have a date?”

“I don’t want to be completely friendless there.”

“Like I said: don’t you have a date?”

“Yes, but-”

“Then there’s really no use for me there, is there?”

“Fine!” Rory sighs. “I give.”   
“Aw, buck up, little camper,” Jess says. “You’ll still have a good time.”

“I guess I have no choice,” Rory pouts.

“You’ll have to tell me all about it, okay?”

“Fine. I’m not going to forget this, though. You owe me.”

Jess laughs. “I’m sure you won’t.”

**

Her dress is  _ perfect,  _ her hair is pretty, and Dean looks great even without a tie. On the drive over to the dance, Rory can’t help but think that maybe, just maybe, she might actually enjoy this.

**

“You don’t want to fight me, Tristan!”   
“Why not?”

“‘Cause I’ll kill you, idiot!”

Rory watches helplessly as Dean wrenches himself out of the grip of a few of her classmates. The look on his face absolutely terrifies her, and she can’t really do anything but follow him when he mutters, “Come on, Rory.” 

Tristan frees himself and runs after them, but stops short when Dean towers over him. “You will not come near her. Ever again.”

Rory swallows down a sob and hurries after Dean. He shoves her coat at her and she puts it on quickly, too scared to speak. She doesn’t like Dean like this, she doesn’t like it at all.

When she steps out of the ballroom, a familiar face is standing there, hands shoved in his pockets. He’s wearing a tie - it’s loose, but he’s wearing one anyway - and his collar is stubbornly not buttoned up all the way. Rory feels relieved, if only for a second. 

“Jess?” She asks, absolutely bewildered.

He gives her a soft smile. “Hey.”

“You came.”

“I did.” 

“W-why?”

Jess shrugs awkwardly; he glances back at Dean, who’s staring at the two of them with an irritated look on his face. “Changed my mind. But sounds like it’s pretty much over, anyway.”

“I guess.”

“Rory,” Dean cuts in. “Let’s go.”

Rory looks over at Jess helplessly. “I gotta...I…” She says lamely, gesturing at Dean.

Jess nods. “Okay.”

Dean wraps an arm around Rory’s shoulders, a little tighter than she would like, but the gesture is sweet, she supposes. 

(She can’t help but look back at Jess before they leave. She sees him scoff to himself and run a hand down his chin. Not knowing what it means, she looks away.)

**

The car ride is completely silent.

**

Dean remains quiet as he parks and buys her coffee from the cart by the gazebo in the center of town. She’s too afraid to ask what his silence means, so she stays quiet too, taking sips of her coffee and staring down at her shoes instead. 

“He has a thing for you,” Dean says suddenly, not all too kindly.

Rory glances over at him with a frown. “What? All he did was insult me and make me absolutely miserable.”

Dean shakes his head. “I wasn’t talking about Tristan. I mean, he obviously has a thing for you too, but no. I was talking about Jess.”

Rory blinks at him in surprise. “Jess?”

“Yeah.” Dean scoffs. “I mean, you said he wasn’t coming to the dance no matter how much you asked. So either you lied to me, or he changed his mind last minute. And you wouldn’t lie about that, right?”

“Right,” Rory assures him. “I wouldn’t.”

“So, something made him want to go, right?”

Rory sighs. “Dean, Jess is just a friend. He doesn’t have a thing for me, okay? And neither does Tristan.”

“God, you can be dense,” Dean says in a teasing voice, but Rory doesn’t find it all that funny. “He has a thing for you. That’s why he tried to pick a fight.”

“Well, at least I had my boyfriend there to defend my honor.”

Dean stops walking. “Boyfriend?”   
“Yeah. I mean...if you’re not - I didn’t mean - I just thought - I just meant, that the whole defending my honor thing, was very boyfriendy, but only in the broadest sense of the word, not as an actual...I don’t think you’re my boyfriend.”

“You are seriously babbling.”

“I do that.” Rory looks away. “I didn’t mean that you’re my boyfriend.”

“Okay.”

“I swear. You’re not.”

“Okay.”

“...Dean?” She asks after a pause.

“Yeah?”

She steals a glance at him nervously. “Are you my boyfriend?”

“In the broadest sense of the word way?”

“No, I mean, like, actual boyfriend. Like if someone asked, I would say, ‘This is Dean, my boyfriend.’”

“I am if you want me to be,” Dean says after a moment of hesitation.

“I do,” Rory replies (before she can lose her confidence).

Dean smiles at her, and her heart skips a beat. “Okay.”

“So, then, it’s settled. You’re my boyfriend.”

“That’s the consensus.”

Rory bites her lip to hold back a grin. “Okay.”

**

She almost falls asleep, curled up with Dean with a book in her hands. The key word, though, is  _ almost -  _ she catches a glimpse of her watch and sits up bolt upright. “Dean.”

“Mm?”

“It’s late. It’s really, really late.”

Dean sits up too, much slower than she’d like. “How late?”

“It’s after midnight,” she says anxiously. “I have to get home. Like, immediately.”

“Rory, calm down,” Dean chortles. “We’ll get you home.”

“Now, please,” Rory says desperately, grabbing her things and not even bothering to button up her coat. “Now.”

Dean stands up and adjusts his coat. “Okay, okay.”

“God, we almost fell  _ asleep.  _ I can’t believe this,” Rory says frantically. She can’t help but think about Jess, his calming presence, how she wishes she could’ve spent a little bit more time with him tonight. “That would’ve been so bad.”

“I don’t know. Why?”

“My mom would freak. She might still freak, I don’t know. Oh, god, and my grandmother…”

Dean hurries down the sidewalk after her. “Do you need me to drive you home?”

Rory turns around and shakes her head. “No, no, it’s fine. You should go home so they don’t kill you or anything.”

Dean nods grimly. “Okay. Goodnight, Rory. Good luck.”   
“Thanks,” Rory breathes before turning and running towards home.

**

When she’s crying to her mom that night, feeling the guilt of yet another fallout between her mother and grandmother and only being able to blame herself, Rory wonders what would’ve happened if she  _ had  _ fallen asleep. The way that rumor about her and Jess made her feel is still fresh in her memory, and she isn’t keen on feeling that injustice again. 

Eventually, Lorelai kisses her on the forehead and says goodnight. “It isn’t your fault, Rory,” she says soothingly, standing by the door. “This is just what your grandmother does. Get some sleep, okay? I love you.”

Once her bedroom door is closed, Rory sniffs and wipes her eyes. Taking down her hair, she realizes that she doesn’t want to be alone, not right now. She needs a friend.

Before she can second guess herself, Rory goes out into the hallway and takes the phone. Back in her room, she dials his number and waits. 

_ “Hello?” _

“Jess?” She asks, just a little desperately. 

_ “Gilmore?” _ Jess’ tired voice asks from the other end.

“Hey.”

_ “What’s wrong?” _

“What do you mean?”

_ “Well, you’re calling at two in the morning. Did something happen, or…” _

Rory mentally curses herself for not thinking about the time. “Oh, my god, I’m so sorry, I didn’t - I didn’t check the time or anything, I-”

_ “Rory.”  _ She stops talking and bites her lip.  _ “It’s okay. You sound upset, though. What’s going on?” _

Rory closes her eyes to hold back her tears. “Tonight was just - it was so bad,” she chokes out. “Tristan and Dean almost fighting, and I almost fell asleep with Dean at Miss Patty’s - it’s this dance studio in my town - and we were reading, and...and it was so late, and my grandmother got angry at my mom again, and - it’s just all my fault.”

_ “It was just a mistake.” _

“My grandmother didn’t see it that way.”

_ “But that’s not on you.” _

“I guess. I just…”

“ _ I get it.” _

Rory sniffs. “What if they never make up?” She asks in a small voice.

Jess hesitates.  _ “Family is tricky,”  _ he says finally.  _ “This is just another bump in the road, right?” _

“But what about your stepfather? And the way he treats you? That’s not just another bump in the road, Jess, that’s…”

Jess sighs.  _ “That’s different. My stepfather...my stepfather is a very angry man, and he doesn’t really love or care about anyone else. Your family isn’t like that. From what you’ve told me, your grandmother cares about you and your mom very much.” _

“I guess.” Rory plays with her comforter as she speaks. “Thank you, Jess. I’m sorry for calling like this, so late.”

_ “It’s okay. I was awake, anyway.” _

“Okay, good. Well, I don’t mean - not  _ good,  _ I’m not saying you not getting sleep is - I mean, like, it’s good that I didn’t wake you up, but-”

Jess starts to laugh quietly.  _ “Rory.” _

Rory blushes. “I was rambling again.”

_ “A little.” _

“Sorry.”

_ “Don’t worry. It’s cu-”  _ He cuts himself off. _ “I don’t mind.” _

Rory smiles to herself. “Thank you, though. I just needed to...talk to someone.” (She just needed to talk to  _ him -  _ but she’d never tell him that.)

_ “Anytime.” _ Pause.  _ “So, what exactly went down at the dance, then?” _

Rory groans and falls back on her bed, earning another laugh from Jess. “How badly do you want to know?” She asks weakly.

_ “More than I’ve ever wanted anything.” _

“Fine. It all started when Paris brought her cousin as a date-”

_ “I’m sorry, she did  _ what?”

“Yeah. And she accidentally announced it to everyone when she was yelling at me.”

She can picture a smile on Jess’ face when he says,  _ “Tell me everything.” _

**Notes for the Chapter:**

> Jess Mariano I would die for you I hope you know


	8. Sanctuary

**Summary for the Chapter:**

> When Richard collapses at the Gilmore holiday party, Rory asks Jess for a favor.

**Notes for the Chapter:**

> I edited this on six hours of sleep so let's hope it's legible lol...anyway enjoy!

The phone rings at 7:55, five minutes before he said he’d call. Pushing her notebook aside, Rory hurries to the hallway to pick it up. “Dean?” She asks excitedly, barely containing a grin.

_ “Hey, Rory.” _

“You’re early.”

_ “Yeah, I couldn’t wait,”  _ Dean says sheepishly.  _ “I was just...excited to call you, you know?” _

Rory does a little dance, earning an amused look from Lorelai, who’s sitting on the couch, watching the new episode of  _ Saturday Night Live.  _ “Well, I appreciate it, so thank you.”

Dean laughs.  _ “So, how’s it going?” _

“I’m good. I was just studying.”

_ “Cool.” _

“What about you? What’s up?” Rory asks, trying to sound casual, and mentally cursing herself.  _ What’s up? Seriously? _

_ “We just had dinner - my mom made pot roast.” _

“Oh, that sounds good.”

_ “Yeah, she’s a good cook.” _

Rory bites at her nail excitedly, taking a seat on an ottoman. “How’s school going?”

_ “It’s okay. Classes aren’t too bad, but I think the PE teacher hates me.” _

“Oh, he hates everyone.”

_ “So I shouldn’t start thinking I’m special, then?” _

Rory laughs. “No.”

_ “As long as we’re on the same page.”  _ There’s an awkward silence for a moment as Rory struggles to find something to say. (They’re still at that awkward,  _ hi-hey-hi  _ phase where she finds herself at a loss for words whenever she’s talking to him.) To her relief, he speaks first.  _ “Hey, uh, I was wondering…” _

“Yeah?”

_ “Do you want to do something tonight? I just got my paycheck from Taylor, so I can totally splurge on something from Weston’s if you want.” _

“Even the fancy cupcakes with the fillings?”

_ “We could even get extras.” _

Rory glances over towards her room, where her notebook is still open on her desk. “Can I take a raincheck?” She asks apologetically. “I’ve got a big test on Monday that I need to study for.”

_ “You can’t skip a night?” _

“There’s a lot of material to cover,” she explains. “But we can totally do it after the test, okay?”

_ “You can’t make time for me, your boyfriend, because of a test?” _

“Well, it’s not - it’s not that I can’t make time for you, it’s just that it’s a really important test.” Lorelai shoots Rory a confused look, to which Rory shrugs. “It’s not personal, Dean, I swear.”

Dean scoffs.  _ “It sure feels personal, Rory. What about your friend, Jess? Would you make time for him?” _

“The only thing I’m making time for is studying. I promise.”

_ “Right.” _

“Why is this making you upset? Did I do something?”

After a moment, Dean just sighs.  _ “No. No, it’s fine. I get it. We can, uh...take a raincheck, right?” _

Rory lets out a sigh of relief. “Thank you for understanding.”

_ “No biggie. I’m a saint, remember? I’ll, uh, I’ll talk to you tomorrow.” _

“Goodnight, Dean.”

_ “Goodnight.” _

After he hangs up, Rory sets the phone down and takes a breath. Crisis averted. 

Lorelai turns to face her. “What was that all about?”

“I don’t know. I think he was a little annoyed that I have to study, but it’s not a big deal.”

Lorelai bites her lip. “Are you sure? It seemed kinda over the top.”

Rory smiles. “Mom. It’s fine. Okay? I’m definitely annoyed that I have to study instead of being with him, too.”

“Okay, okay…” Lorelai sighs. “I trust your judgement. You’d tell me if it was worse.”

“I would, mom, I promise.”

“Good.” Lorelai smiles. “Now get back to studying. I’m expecting at least a smiley face on the top of your test when you bring it home.”

“Would a sticker suffice?”

“I suppose. As long as it’s sparkly and/or scented.”

“I can’t make any promises.”

Lorelai pouts. “Fine.”

Rory glances at the TV. “Who’s hosting?”

“Kate Hudson. Musical guest is Radiohead.”

“Oh, cool. Tape that for me, would you?”

”Do you even have to ask?”

**

Rory feels a little guilty leaving her mother home alone to go to her grandparents’ holiday party, but Lorelai assures her that it’s okay. “Go have fun for the both of us,” she assures her daughter. “And steal me some apple tarts.”

The dinner is fine - of course it’s not going to be the same without her mother there - but it goes well enough. That is, until her grandfather collapses.    
This might just be the single most terrifying moment in her life, Rory thinks, sinking down into one of the chairs in the waiting room. Her legs are shaking, she realizes. She wasn’t even aware of that until she sat down. 

Taking a shuddering breath, Rory dials her mother’s number; she waits for one ring, two, three -  _ “Rory? How’s the dinner going?” _

“Mom?” Rory closes her eyes, trying not to cry. “Mom, grandpa, he-” 

_ “What happened?” _ Lorelai demands after Rory cuts herself off. 

Rory sniffs, taking another deep breath. “He collapsed. At the party. We’re at the hospital right now, and, uh...yeah.”

She hears Lorelai take a shuddering breath on the other end.  _ “Okay. Okay, thank you, Rory. I’ll, uh, I’ll try to get there as soon as I - shoot, you took the car. Um…I was at the diner, but Luke kicked everyone out when Taylor brought in the carolers...I...” _

Rory doesn’t think she’s ever heard her mother at a loss for words before. An idea hits her, thank god, so she clears her throat and says, “I’ll get you a ride, okay? It’s gonna be fine,” she adds, wishing she could believe it.

_ “You sure?” _

“Yeah.”

_ “Okay. I’ll be at home.” _

“Okay.”

_ “Love you, kid.” _

“I love you, too, mom.”

Rory hangs up, feeling no relief as she dials his number. The phone rings several times, and then it’s just  _ Hi, this is Dean Forester. I can’t come to the phone right now, so you know what to do. _

She tries again, but she gets  _ Hi, this is Dean Forester. I can’t come to the phone right now, so you know what to do. _ And again, and again, but it’s just  _ Hi, this is Dean Forester. I can’t come to the ph- _

Rory hangs up, resisting the urge to throw her phone on the ground in frustration. Okay. Okay, it’s going to be fine. She needs to think of someone who would be fine doing this for her, that wouldn’t get angry or say no or-

She’s dialing his number before she fully realizes what she’s doing. He picks up after two rings.  _ “You’ve reached Radiohead. Currently, we’re dealing with a bit of a creep situation, someone took the money and ran, but-” _

“Jess, that isn’t funny,” she says harshly, but immediately regrets it. “Sorry. Under normal circumstances, that’s actually kinda funny, in a dumb way, but...not right now.”

_ “Sorry. They just performed it on Saturday Night Live.”  _ He pauses. _ “What’s wrong?” _

“Can you please do me a favor?” Rory asks with a wince. 

_ “I can’t make any promises. What do you need?” _

“I, uh…” Rory taps her foot on the ground anxiously, trying to work up the nerve to ask him. “I was at my grandparent’s holiday dinner, and my grandfather collapsed. We’re at the hospital, but my mom wasn’t there, and I need someone to - and she needs a ride. I already tried calling Dean, but he wasn’t picking up, and I’m really sorry for asking this of you, I just - I didn’t know who else to call,” she says, her voice breaking at the end.

There’s silence on the other end for a moment.  _ “You live in Stars Hollow, right?” _

Rory nods, but then mentally scolds herself because of course he can’t see her. “Yeah.”

_ “Okay. Just, uh, give me the address of your house.” _

“Thirty-seven Maple Street.”

_ “Okay.” _

“Wait, don’t you need to know how to get to Stars Hollow?”

_ “No, I know where it is.” _

Rory’s brow furrows in confusion. “How?”

_ “I’m a man of the world, Gilmore, remember?” _

“Okay, when guys say that, it usually means that they’re a philanderer or something.”

Jess laughs slightly.  _ “You’ve met me. Do I have anyone to philander with? Or to philander against?” _

“Is that even grammatically correct?”

_ “Beats me. You’re the smart one, remember?” _

Rory smiles a bit; admittedly, she feels a little bit better. “Thank you, Jess. Thank you so much. I owe you big time.”

_ “Consider this a repayment from not going to the dance when you asked me to.” _

“You remember that?” Rory asks, surprised he would remember a throwaway comment she made a week before.

_ “I have a good memory. Thirty-seven Maple Street, right?” _

“Yeah.”

_ “I’ll be there as soon as I can.” _

“Thank you.”

_ “No problem.” _

She hangs up, letting out a breath she’s been holding for what feels like the past hour. She relaxes a bit, leaning back in her seat. She tries to tell herself that it’s going to be okay, but for once in her life, she can’t find any way to be positive about this.

**

She calls Luke a few minutes after.

**

“Rory?”

Rory opens her eyes - she must have dozed off - to see Lorelai hurrying towards her, a scared look on her face. Rory gets up and immediately falls into her mother’s arms. “Mom, it was horrible, I-”

Lorelai smooths down her hair and kisses the top of her head. “I know. I’m sorry you had to deal with it alone.” She pulls back and grimaces. “Alright. Let me deal with your grandmother.”

When Lorelai steps aside, Rory makes eye contact with Jess. He stands there, kind of awkwardly, but there’s a kind look on his face that almost breaks her.

Rory rushes over to him and throws her arms around his neck, holding him tightly. Jess tenses, and slowly wraps his arms around her, holding her close. She buries her face in his shoulder, breathing in that scent that is just so  _ Jess.  _

“Thank you,” she mumbles, her voice muffled. “Thank you.”

She feels his head move slightly, until she can feel his breath by her ear and hear him murmur, “Of course.”

She holds him a little tighter. Jess must pick up on the fact that she’s unwilling to let go, because he just sighs and strokes her hair once. She relaxes a bit; there’s just something about him that stabilizes her and makes her feel so much better.

She’s unsure of how long they’ve been standing like that, but then she hears her mother call her name, so she pulls away a little too quickly, her face flushing pink.

“Rory? You wanna go in and see him?” 

Rory looks from Jess to her mother and nods. As she’s walking to the hospital room, she hears her grandmother say, “Is that Dean?”

“No, mom, that’s Jess. Her friend from school, remember?”

“Oh, yes. Jess. Odd name for a boy, don’t you think?”

Rory looks over her shoulder and gives Jess an apologetic look. 

He just smiles and shakes his head.  _ What can you do?  _

**

When she leaves the hospital room, she’s surprised to see that Jess is still there. He’s sitting in one of the seats, reading, but when she approaches him, he looks up and smiles.

“How is he?”

“He’s gonna be okay,” Rory says, a weight lifting off her shoulders as she says the words. 

“I’m glad.”

“Thank you, again, for...for everything. I just...I needed…” She trails off.

“It’s okay.”

She smiles. 

Jess stands up, pocketing his book. “I brought you something,” he says, handing her another book.

She looks down at the well-worn book.  _ “The Catcher in the Rye.  _ This is my copy.”

Jess nods. “I took it from your room when I picked you up. Don’t worry, I asked your mom before going in there,” he adds when he sees her mouth open to speak. “It’s one of your favorites, right?”

She glances up at him, bewildered. “How did you know?”

“It was one of the most worn ones. And, knowing that you’re a book snob, it wasn’t hard to guess that it’s been read a lot of times.”

“Hey, I am not a book snob.”

“You are. But it’s okay,” he adds with a sly smile. “I like it.”

She blushes. They stare at each other for a moment, but she looks back down at the book, breaking the tension. “So, uh…”

Luckily, she’s saved from having to say anything when her mother comes over. “Hey, honey. How are you doing?”

“As good as I can be,” Rory says. “You?”

“Yeah, same here.”

“I’m gonna get going,” Jess says to Rory. “Unless you need anything else…?”

Rory shakes her head. “I’m good. Thank you, again.”

Lorelai nods. “Yeah, thanks for the ride. I really appreciate it. I don’t plan on this happening again, though, so don’t start thinking you can charge us.”

Jess smirks. “I was just about to start a taxi service, actually.”

“You’ll have to find some new clients. The Gilmores are closed for business.”

Rory rolls her eyes and goes to hug Jess again. “I’ll see you at school,” he says in her ear.

She nods. Stepping away, she gives him a quick kiss on the cheek before pulling back. “Drive safe.”

He smiles, turns, and walks down the hall and out of sight.

**

Luke comes in about ten minutes later with coffee. Lorelai nearly tackles him to get to the coffee, but once she has a sip she hugs him for almost as long as Rory hugged Jess. Smiling to herself, Rory turns away and drinks from her own. 

(She knows she said that her mother can’t date Luke, but admittedly, there’s something there. Glancing at her grandmother, Rory knows that the only people who don’t see it are Luke and Lorelai themselves.)

**

“So, you called Jess?”

Rory looks over at her mother, whose eyes are still on the road. “Yeah. Why?”

“It was very nice of him.”

“Yeah, it was,” Rory agrees. “But why did you bring this up?”

Lorelai glances over at her daughter, looking oddly concerned. “You didn’t think about asking Dean?”

“I did, but he wasn’t answering his phone, so I called Jess. Mom, what’s this about?”

Lorelai shrugs. “I’m just making sure we’re on the same page here. But, uh, are you going to tell Dean?”

“Probably. He’s my boyfriend. Why?”

Lorelai hesitates. “Rory, honey, you’d tell me if you were feeling...unsafe with Dean, right?”

Rory stares at her mother, confused. “Of course. I tell you everything, remember?”

“Yeah. Yeah, I know.”

“Good.” Rory turns and faces front in her seat. “And yeah, I would.”   
“Okay.”

“Okay.”

(This gets her thinking, though. Is Dean going to be okay with this?) 

(The thought leaves her a little uneasy for the rest of the car ride.)


	9. High Fidelity

**Summary for the Chapter:**

> Paris spreads a rumor about Lorelai and Mr. Medina. Jess and Rory officially take their friendship outside of Chilton.

**Notes for the Chapter:**

> NOTE: Some dialogue is taken from 1x11.

If she’s being completely honest, Rory was  _ not _ happy when her mother first told her that she was dating Mr. Medina. It was weird and awkward and made her worry about what would happen if her classmates found out. 

Now, however, things have started to change. Rory admittedly really likes Max being a part of their lives outside of school - not that she would tell anyone. She hasn’t even told Jess. 

(And she’s calling him  _ Max  _ now. Is it possible that maybe, this guy might stay?)

Rumors about Paris’ parents have been spreading lately. Rory’s noticed, but she hasn’t said anything, she doesn’t think it’s her place to - or is that just an excuse to stay out of it? She doesn’t know if half of them are true, but Jess says most of them probably are, and Rory knows Paris would just take her involvement the wrong way. If she angers Paris, Paris will do something even worse to her, so Rory just keeps her mouth shut. At least things are finally quieting down at Chilton when it comes to Rory. She doesn’t need a retaliation from Paris that’ll just shake everything up again.

Turns out, that’s exactly what she gets. 

**

The lunch room is definitely louder than usual today. Maybe there’s a new rumor about Paris or something, but some information is going around that’s making all of her classmates rowdy.

Rory’s reading Emily Dickinson - Jess had to stay behind in their last class, so it’s just her right now - when Tristan comes over and blows her a kiss. Confused, but not surprised, Rory tries to go back to her book, but, of course, there’s no rest. 

Paris comes over with a smug look on her face and stands over Rory. 

“What’s going on?” Rory asks, utterly bewildered, and very suspicious.

Paris smirks. “Oh, everyone’s just talking about the mom that Mr. Medina was seen kissing just now.”

Rory feels her blood go cold. “What?”

“And the weird thing is,” Paris continues, “she looks like  _ your _ mom.”

Poker face, poker face. “What are you talking about?”

“Your mom, Mr. Medina, mouths open - I saw them.” Paris smiles. “How’s the coleslaw? Good?”

Rory watches her walk away, feeling her stomach drop what feels like ten stories. She can feel heads turning towards her, and she wishes the floor would open up and swallow her whole. 

A few minutes later, the chair next to her is pulled back and Jess takes a seat next to her. “Mrs. Ness takes her sweet time,” he says apologetically. When he catches the distressed look on her face, his brow furrows in confusion. “What’s up with you?”

Rory glances around before leaning in and whispering in his ear. When she pulls back, Jess stares at her with a dumbfounded expression.

_ “What?” _

Rory nods grimly. “Apparently, he and my mom thought that his classroom - you know, the one with the windows - was the perfect place for a little make-out session.”

Jess scoffs in surprise. “Wow. And did you know that they were…”

Rory nods.

“And you didn’t tell me?” Jess shakes his head. “God, you really think you know a person…”

Rory scowls and elbows him in the side. “Oh, shut up.”

Jess bites back a laugh for her sake. “Okay, okay. I’m done.” He looks at her for a minute. “This is really stressing you out, huh?”

“Well, I’m finally the center of attention again,” Rory says bitterly. “Just what I wanted, right?”

Jess bites his lip. “Well, you know,” he says after a moment of hesitation, “things weren’t exactly  _ quiet _ when I started here, either.”

Rory looks up at him with a frown. “What?”

“Yeah. I mean, a kid starting here in the middle of April? My  _ stepbrother  _ took it upon himself to tell everyone how my mom is an alcoholic - while not even admitting he was my stepbrother. Classy.”

“I’m sorry.”

Jess shrugs. “Paris wasn’t particularly threatened by me, so no one spread any other rumors about my family. Actually, since you’re really the first person I’ve actually talked to here, I don’t know if anyone actually  _ knows _ who my stepfamily is.”

“Who’s your stepfamily, then?” Rory wonders, hopeful.

“So, how’s the coleslaw?” Jess asks, ignoring her question. “Is it any good? I need to get some food.”

“Very evasive of you.”

“Or maybe I could get the chicken pot pie. Are they serving that today?”

Rory sighs. “Okay, fine. Forget I asked.”

Jess just smirks at her.

“Hey, did you save me some jell-o?” 

Rory looks up to see her mom hurrying over, beaming like nothing is wrong. Rory glares at her and storms off, hoping Jess will forgive her for her rude exit, Lorelai close behind her. 

**

Another rift between her mother and grandmother? Lovely. Just what she needed. 

Rory calls Jess when she gets home from dinner, venting to him about everything that happened. When she’s done, Jess sighs.

“Maybe yell at Paris on Monday,” Jess offers. “That’ll help you get it all out of your system.”

She laughs and when they say goodnight, she feels just a little bit better.

**

Saturday night, Dean comes over and takes her to Weston’s. He buys her a danish and a coffee, smiling when she consumes them at a faster-than-average rate.

“How was your week? I feel like I’ve barely seen you at all,” Dean says. 

Rory nods. “I’ve been busy,” she says, wiping her face with a napkin. “The past week or so has been a nightmare, so just be glad you weren’t there.”

Dean frowns. “What happened?”

“God, where do I start?” Rory laments. And it’s true - she’s not sure where to begin. So much has happened, she hasn’t gotten to telling Dean about the rumor that Tristan spread about her and Jess. “My grandfather collapsed at a dinner party,” she decides to say. “He’s okay now, but..it was scary.”

“Wow. I’m sorry. That must’ve been terrifying.”

Rory nods and bites her lip. “It was. And my mom wasn’t even there, it was just me and my grandmother at the hospital - I had to ask Jess to bring my mom there, and I was just so afraid that something would happen to my grandpa before my mom got there.”

Dean’s eyes narrow. “You called Jess.”   
“Yeah. I’m just lucky he said yes. Otherwise, I don’t know what I would’ve done. I guess I could’ve called Luke, though. I don’t know.”

Dean’s lips are pursed together as he looks at her with an expression that makes her feel a little smaller than usual. “Why didn’t you call me?”

“I did,” Rory explains, “but you didn’t pick up, and I wasn’t sure what else to do except to-”

“To call Jess,” he finishes for her.   
She nods. “Yeah.”

He scoffs. “So, what, is he your backup or something? In case this doesn’t work out?”

Rory blinks a couple times in confusion. “What?”

“A backup is like a reserve, you know, someone you can use as a replacement if you have to,” Dean says condescendingly. 

Rory’s stomach drops a bit. “I know what a backup is,” she mumbles, choosing to stare at her empty plate rather than look at him.

“Well, you sounded confused, so…”

Rory takes a deep breath. “He’s not a backup, Dean. He’s a friend. I’ve told you this a million times.”   
“You weren’t very clear here. That’s what it seemed like.”

Rory bites her lip. “I know. I’m...I’m sorry.”

Dean smiles warmly. “It’s okay. I know you didn’t mean to hurt my feelings.”

“Good.” Rory smiles back, but there’s still an uneasiness in her that won’t go away. “Because I would never do that on purpose.”

His expression brightens. “I know. You look really nice, by the way,” he adds. “With the headband and the sweater and all.”

Rory grins. “Thank you.”

“Do you want some more coffee?” Dean offers, already taking out his wallet. “You look a little low there.”

“Don’t mind if I do.” She starts to get up, but Dean holds up a hand and smirks. 

“I’ve got it.”

Rory blushes and settles back into her seat. As Dean goes to the counter and orders her another coffee, she feels the uneasiness fade away. It’s probably just nerves, she thinks to herself as he sits back down and grins at her. They’ve only just begun to date. Besides, they’re both figuring out what the other one is like and how to treat them, right? 

Her mother said to tell her if she felt unsafe, but she  _ doesn’t  _ feel unsafe, so there’s no cause for alarm. She really likes Dean, and he really likes her (a thing she still can’t quite fathom), and that’s the most important thing.    
She reminds herself of that for the rest of the night.

**

Lorelai and Max break up the next day.

**

Rory comes to school the morning after the breakup sullen and exhausted from comforting her mother all night. She’s got a bit of a headache, but it’s nothing that coffee can’t fix, so she downs a cup extra on her way to school. Jess gives her a weird look when she meets him outside the school, but he doesn’t comment on any of it.

At the end of the day, Jess pulls Rory aside, looking concerned. “Okay. What is going on with you today? You look...hungover, and I know for a  _ fact _ that you don’t drink.” 

She gives him a look. “How do you know that?”

“You’re the poster child for advocacy against underage drinking. Now tell me.”

Rory sighs. “My mom and Ma - Mr. Medina broke up,” she mumbles, pulling her sweater over her hands anxiously. 

“Oh.” Jess rubs her arm comfortingly. “I’m sorry. I know you were getting attached.”

Rory shrugs, but she can’t cover up her sniff. “It’s okay. Just...sucks, I guess.”

Jess nods. “I get it.” He pauses. “Hey, do you have any plans after school today?”

Rory shakes her head. “Just homework.”

The corner of Jess’ mouth quirks up. “Well, you do now.”

She looks up at him in confusion. “What?”   
“I’m taking you out.”

“Again, I must repeat: what?”

Jess rolls his eyes. “You. Me. George’s Pizza Restaurant. A table. Some chairs. A nice, big, round pizza with your choice of toppings. Maybe some cokes. You get the picture?”

Rory elbows him in the side. “It’s crystal clear.”

“So, what do you think?” Jess asks, playing with the strap of his bag. Rory understands his hesitation - besides him bringing her mother to the hospital, they haven’t exactly taken their friendship out of Chilton. There’s some checkpoint they’d be passing, she’s sure, but she grins and eases his nerves.

“I think I can swing it.”

“Good.”

**

Jess is waiting for her when school is done. He shoots her a smile as they wordlessly walk out of the building. She starts to walk down the sidewalk, but Jess takes hold of her wrist. “Where are you going?”

“Are we not walking?” She asks.

Jess looks at her, amused. “If you want to talk all the way over to the Historic District, be my guest. I’ll see you in a week.”

She looks at him flatly. “So how are we getting there, then? The bus?”

Jess reaches into his pocket and pulls out his keys. “I was thinking more along the lines of driving.”

“Oh.”

“If that’s okay with you,” he adds.

“Are you a good driver?” She asks skeptically.

“I’ve won some awards.”

“Oh, shut up.”

“Hey, I’ve never hit anyone, been in an accident, or injured anyone,” Jess says. “Does that fulfill your requirements?”

“Fine.”

She follows him to the parking lot, where he stops in front of a black BMW. “Your ride, m’lady,” he says, opening up the passenger door.

“Hey, you said you’ve never been in an accident,” Rory says, giving him a look.   
Jess looks at the dent that she’s pointing at. “I haven’t. I did that on purpose.”

“I’m sorry, what?”

Jess half-laughs. “I told you I fucking hate this thing. My step-dad will spend a bunch of Gs on it, but he’s a cheapskate when it comes to repairs. He was  _ pissed,  _ but the look on his face whenever he sees it is golden. Now, are you getting in the car or what?”

Rory grumbles under her breath and gets in the passenger seat. Jess starts the car and glances over at her. “Are you doing okay? With your mom and Mr. Medina and everything?”

Rory gives him a grateful smile. “I’m sad, but I think my mom’s worse off.”

“Well, I…” His jaw clenches, and she notices that his grip on the gear shift tightens. “I’m, you know…”

“Are you trying to say that you’re here for me?”

His head dips slightly - the most imperceptible of nods. 

Rory smiles. “Thank you, Jess.”

He turns to fully look at her, and there’s a gleam in his eyes that makes her stomach bottom out, but it isn't from dread. It’s a different feeling, a new one, but she doesn’t dislike the way he makes her feel one bit. 

**

“I cannot  _ believe  _ you would say that.”

Jess pauses mid-bite and laughs. “What, are you saying that I’m wrong?”

“I’m saying that Jane Austen and Bukowski are two entirely different genres.”

“Yes, but genre is different from purpose.”

“Jane Austen wrote about, what, Victorian England? Bukowski wrote about the Beats.”

Jess sighs. “So, they both wrote  _ about _ one audience, but look at how widespread their books have become.”   
“What do you mean?”

“You and I, right?” Jess says. “I’m from New York. I started smoking at age fourteen. On all accounts, Bukowski wrote for people like me. And you’re a small town girl who worked her ass off to go to private school and you, I don’t know, have manners. Austen would be for you.”

“I’m sorry, what?”

“I enjoy Austen. You’ve read Bukowski.”

Rory sighs. “That’s true.”

“So, then, they’re not for any specific audience. These books expose you to a world you would never have known, right?”

“All right, you’ve made your point.” Rory’s about to keep talking when her pager beeps. She looks down - it’s Dean.

Jess frowns at her. “Everything okay? That’s, what, the fifth time?”

“Six if you include the phone call.”

“Who is it?”

Rory bites her lip. “Dean,” she admits.

“Ah, the infamous boyfriend.” Jess reaches over and takes a sip of Rory’s coke. “What’s he want?”   
“Dunno.” Rory dips a fry in his ketchup and eats it. “It’s not a big deal, Jess.”

“Okay,” Jess says, and he doesn’t push any further. He smiles at her. “Have I mentioned how nice it is to be able to talk to someone about anything remotely literary?”

“What, your step brother isn’t a big reader?”

Jess scoffs. “No one in that family is.”

“You’ve never made any friends that read?”

“I’ve never made any friends besides you,” Jess says, all-too-casual.

Rory frowns. “That’s sad.”

“Not really,” Jess replies with a shrug. He takes another slice of pizza. “Never really needed them.”

Rory opens her mouth, then closes it, unsure of what to say. She feels like the conversation has turned serious, but Jess doesn’t seem to feel the same way. He takes a bite of his slice, but Rory’s still at a loss for words.

Jess swallows his food. “Spent some time with Summer before school started this year - I think the last book she read that wasn’t for school was  _ Magic Tree House.” _

“Aw, those were good.”

Jess nods. “I guess.”

“And what do you mean, spent time with?” Rory asks, her curiosity getting the best of her.

Jess looks at her amusedly. “I’m sure you can figure it out.”   
“What, were you two friends or something?”

“I wouldn’t put it like that, no.”

“Then what?” Rory questions. “You two never even talk. What could you possibly have-”

Jess gives her a look. “Sex, dear.”

“Oh.” Rory turns pink and stares down at her plate. “Oh, so you two-”

“Yep.” Jess takes another sip of her coke, seemingly unbothered. 

“Over the summer.”

“Mhm.”

“Summer with summer?”

Jess lets out a laugh. “I suppose so.”

Rory squirms a bit in her seat, the thought of Jess with  _ Summer  _ making her feel a little strange, for some reason. “The same Summer that Tristan is ‘dating?’”

Jess nods. “The very same.”   
Then, something hits her. “Is that why you guys hate each other so much? You and Tristan.”

Jess hesitates for a moment. “You could say that’s a reason.”   
It feels a little anticlimactic. “Are there others?”

“I mean, he’s a grade-A tool.”

“That’s true, he is.”

Jess shoots her a smile. “Come on, enough about me. I’m really not interesting enough to prompt a conversation of this length.”

Rory rolls her eyes. “Just one more thing.”

“Shoot.”

“Are you and Summer...are you still…” She trails off.

Jess shakes his head. “Nope. Ended when the summer ended.”

“Oh.” Rory has to admit, she feels a little relieved. “Okay.”

“Why?” Jess asks.

“Why what?”

“Why do you care?”

Rory feels a blush creeping up her face. “I don’t.”

“Okay.”

“Okay.”

They sit in silence for a minute until Rory’s phone rings. Jess gives her an odd look when she ignores it and just keeps drinking her coke.

“You gonna get that?”

Rory shakes her head. 

Jess looks like he wants to say something; instead, he just takes another bite of his pizza.

It’s not so bad, she thinks, being here with Jess. Even when they’re sitting there, quiet, she doesn’t feel that urge to fill the silence. There’s a contentedness she feels here that she hasn’t felt before, not even with Dean. 

And it’s a good feeling to have. 


	10. Please Kill Me

**Summary for the Chapter:**

> Mr. Medina assigns a group project. Jess and Rory continue to bond.

**Notes for the Chapter:**

> Sorry it's been double the amount of time between chapters this time around. Can't promise I'll be consistent the whole time, but I'll keep trying. Anyway, hope you guys like this one!

Rory gets to school a little early the next day. No particular reason, but she woke up before her alarm, and the bus got there early, so here she is, getting off the bus forty-five minutes before her first class.

To her surprise, when she enters the courtyard, a familiar face is sitting on one of the brick half-walls. She smiles to herself and jogs over to him.

“Jess.”

He looks up and takes off his headphones. “Well, you’re here early.”

“Yeah. Had a good morning.” 

“And we all know how rare those are.” He grins. “I guess that pizza agreed with you.”

She hops up and sits next to him. “Yeah, yeah. It was good, I’ll admit. Although I don’t understand how you prefer plain cheese pizza with no toppings.”

“You want a lame explanation or one that’ll make you feel bad for asking?”

Rory rolls her eyes. “Just be honest with me.”

“My mom could never afford extra toppings,” Jess says with a shrug. “So, we always got plain cheese. Guess you get accustomed to it.” He shakes his head when he sees the look on her face. “See, I told you it would make you feel bad for asking.”

“Oh, and I’m known for taking your advice?”

“Point taken.” Jess looks at her amusedly. “So, you work out everything with the boyfriend?”

She frowns. “What do you mean?”

“All his pages and calls yesterday. Everything alright there?”

Rory nods, but her heart isn’t really in it. “Yeah. I just forgot to tell him that we were getting pizza after school, and he was waiting for me at the bus stop.”    
“Huh.” Jess plays with the strap of his bag absentmindedly. “Did you have plans, or…?”

She shakes her head. “Not really.”

Jess nods slowly. “I’m glad everything’s good.”

“Thanks. Me, too,” she says, somewhat puzzled. “Speaking of Dean, I have something to tell you.”

He raises an eyebrow.

“So, my friend Lane from back home had a thing for this one guy, right?”

“As one does.”

“And the guy is friends with Dean, so I got him to set up a double date.”

“Well, fill me in.”

She tells him about the double date, complete with her mother finding out. When she’s done, Jess bursts out laughing, something that surprises her but delights her as well. 

“Okay, it’s not  _ that  _ funny,” she reprimands him after a minute.

“Oh, I must disagree. It’s hilarious.”

She glares at him. After another moment, he sobers up, but he’s still grinning. His crooked smile makes her heart skip a beat.

Rory clears her throat. “What’re you listening to?” She asks, gesturing to his walkman and headphones.

“Beatles.”

“Really? Would’ve guessed you’d reject them on principle.”

Jess shrugs. “They had some good stuff.  _ Help  _ is their best.”

Rory smiles. “That’s a good album.”

“Yeah,” he says with a nod. “I bet ‘I Need You’ is your favorite. _I could never really live without you.”_

“Nope. ‘I’ve Just Seen a Face.’”

“Huh.”

_ “But as it is, I’ll dream of her tonight.” _

There’s a ghost of a smile on his face as he looks at her, and there’s that familiar sensation in her stomach that she gets whenever he does. 

“What about you?”

“‘Yesterday.’”

“God, when I was little, I used to cry every time I heard that song.”   
He stares out in front of him. “It’s a sad one.”

“Then why do you like it?”

“It’s beautiful,” Jess says after a pause. “Songs about love and loss usually are.”

It’s such a serious thing for him to say, she thinks, and she’s reminded of what she overheard when he was talking to Medina. He said that Jess was a writer, and while she’s never read anything he’s written, she can see it in him in moments like these. 

Wordlessly, Jess takes his headphones from around his neck. His hands brushes against hers, which makes her breath hitch; he puts one end in her hand and brings it up to her ear, holding the other side up to his. “Here,” he says, his voice husky. He hits play, and they sit there, listening. 

_ I said something wrong, now I long / for yesterday… _

**

Rory gives Jess a warning glare to stop snickering at her group arrangement - but she doesn’t have to for long. Him being paired with Tristan and a couple other guys shuts him right up. 

Outside the classroom, after offering up her house for the group meeting - she’s surprised Paris agreed to it, frankly - Jess trudges out of the classroom looking sullen. She almost goes to him, but Tristan slides in between the group of girls, blocking Rory’s path. She makes eye contact with Jess, who rolls his eyes.

“Hey, Paris,” Tristan says in that voice he saves only for flirting. Rory is disgusted - the way he leans in, invades Paris’ personal space. It feels all too familiar. “You know, I was hoping we’d be in the same group.”

“You were?” Paris asks, sounding surprised.

“Yeah. We’d made the long hours of studying go by a lot faster,” Tristan says. From behind him, Jess makes fake vomiting faces; Rory has to hold back a laugh as to not alert Tristan. “Plus, come on - you and me on the same team? We’d wipe the floor with the others. I guess we’ll just have to pair up on something else.”   
Paris is smiling more than Rory has ever seen. “That would be good,” she says, almost hopeful.

“Yeah, it would.” Rory rolls her eyes at him. “I’ll see you later. Bye, Madeline. Bye, Louise.” No  _ bye, Mary.  _ Rory can’t help but feel a little relieved. 

“I’ll see you at  _ my  _ house,” he sneers at Jess, before walking away.

Jess shoots a glare at Tristan’s retreating back. Rory fidgets a little bit, not knowing what to make of it. The new knowledge of Jess’  _ thing _ with Summer definitely explains the tension, but she also knows it feels a little too...easy. Mysteries usually have much bigger answers, and she has a feeling that there’s one big thing that Jess isn’t telling her.

**

After her mother invites them all to the concert, Rory slips into her room and dials Jess’ number. 

“I need your advice on something,” she says the moment he picks up.

Jess chuckles.  _ “Is the group project that bad, Gilmore?” _

“No, it’s actually not bad. We’re sort of getting along.”

_ “Who would’ve thought?” _

“Right?”

He laughs again.  _ “So, what do you need my advice on?” _

“My mom decided to take all of us to see the Bangles in New York.”

_ “What, is it 1986 again?” _

She rolls her eyes. “It’s a reunion tour,  _ Mariano.” _

_ “My mistake.” _

“But you’re from New York, right?”

_ “Born and raised, or something like that.” _

“Do you have any tips?” She asks. “I’ve only been there for shopping and stuff. Are there any good places to eat, or things to look out for, or…?”

Jess hesitates.  _ “Where’s the concert?” _

“Radio City.”

_ “There’s bound to be hot dog vendors around there. You can’t go wrong with those. Although, Paris might freak out. She’s not exactly trusting when it comes to the big cities.” _

“Probably. But that’s a good idea. Thanks.”

_ “Hey, anytime.” _

She sits down on the edge of her bed. “Jess?”

_ “Hm?” _

She picks at a loose thread from her comforter. “Tell me more about New York.”

_ “What do you want to know?” _

“Anything.” She bites her lip. “Everything.”

She knows he’s smiling when he says, quietly,  _ “As you wish.” _

**

When they finally hang up, Rory falls backwards on her bed and stares at the ceiling. This odd feeling she gets when talking to Jess has only become more prominent as time passes, and it’s killing her, not being able to define it. But the feeling itself?

The phone rings, and Rory sits up, taking a breath. “Hello?”

_ “Hey, Rory.” _

She grins to herself. “Hey, Dean.”

_ “So, what’s going on?” _

“Just this group project. It’s not really that exciting. We’re going to see the Bangles, though.”

_ “Is that for the project?”  _

“No, just for bonding or something, I guess. It was my mom’s idea.”

Dean snorts.  _ “Bonding?” _

“I don’t know, it could be nice. Things have been getting with Paris and her friends, so...this could be a chance to get closer.”

_ “I guess. Let me know how it is, then.” _

She glances over at her nightstand where  _ The Tell-tale Heart and Other Writings  _ sits. “I will.”

**

Jess listens to every detail about the concert with a grin on his face.

**

When she tells Dean, he nods, looking bored. When she’s done, he smiles and asks her if she wants another order of fries. 

“You wanna hear about the setlist?” She asks instead of answering his question.

He shrugs. “Sure. I don’t really know any of their songs, though.”

“Oh.” She stares down at her empty plate for a moment before looking up at him with a fresh smile. “Okay. Let’s get more fries.”

**

“Alright, class dismissed. I’ll hand back your papers next class, so  _ please  _ do not leave any more notes in my mailbox about them. Mr. Mariano, a moment, please?”

Rory glances over at Jess with a questioning look, to which he just shrugs. She gestures over to the door, as if to say,  _ I’ll wait out there.  _ He nods in acknowledgement.

Jess approaches Mr. Medina’s desk as everyone files out, Rory watching subtly from outside the classroom. “You wanted to talk.”

Mr. Medina nods. “I was reading over your latest paper, and I wanted to discuss a few things with you.”

Jess’ jaw tightens. “What did I do wrong?”

To Rory’s surprise, and surely Jess’ as well, Mr. Medina  _ laughs.  _ “Actually, there wasn’t anything wrong with it.” He pulls out Jess’ paper and slides it towards him, a big red ‘A’ at the top. “Good job, Jess.”

Jess stares down at the paper in disbelief, but assumes a neutral expression as quick as he can. “Huh.”

Mr. Medina smiles. “You’re intelligent, Jess, more than you give yourself credit for. And this time, you put in effort, and look where it got you.”

“Could be a fluke.”

“It could be, but I don’t think it is.” Mr. Medina leans forward in his chair. “You’ve been more attentive in class, doing your homework, and putting effort into your assignments. I don’t know what prompted this change, but it’s good. You could really turn all of it around, Jess, if you let yourself.”

Jess continues to stare at the paper before him. “It was just one paper.”

“One ‘A’ can turn into more. I want to see you succeed, Jess. Like I said before, you’re a natural writer. Maybe someday, there’ll be a book with your name on the cover.” Jess scoffs. “But for the time being, keep writing like this. Pass the class. Then, we’ll see where you’re at.”

Jess glances up at Mr. Medina hesitantly. “What would it take for me to pass the class?”

Mr. Medina looks surprised, but he shakes it off. “Well, you’re averaging at an ‘F’ currently, but I’ll be assigning another paper next week, and there’s the quiz tomorrow and the test in two weeks. Study - maybe borrow notes from a friend, perhaps Miss Gilmore - and put as much effort into the next essay as you did this one.”

Jess nods slowly. “Okay.”

“I’m glad to see you taking this seriously,” Mr. Medina says kindly. “You’ve got a lot of potential. Don’t waste it.”

Jess raises an eyebrow. “Don’t push it.”

Mr. Medina laughs. “I’ll let you maintain your reputation. As long as you don’t start reading during my class again; that’s my only condition. Besides, reading books about punk rock doesn’t exactly fit the theme of an English class.”

“What about the Beats?”

“I do love Kerouac, but unfortunately, I don’t know if he and Shakespeare get along.”

“You never know. Shakespeare might’ve had a broader taste than people give the man credit for.”

Mr. Medina looks at him amusedly. “You might be right. You’ve got a good conception of these authors, Mr. Mariano.”

“Yeah, well.”   
“I have something for you.” Mr. Medina turns to the shelf behind him and pulls out a book, handing it to Jess. “I think you might enjoy it.”

_ “The Motion of Light in Water?”  _ Jess asks, turning the book over in his hands.

Mr. Medina nods. “Try it. I think it’s up your alley.”

Jess nods, slipping the book into his bag. “Thank you,” he says, and it’s awkward - Rory’s sure it’s not something he’s used to saying.

“Of course. I’ll see you in class tomorrow.”

Jess nods again and gets out of the chair, exiting the classroom. Rory moves back a little, but Jess eyes her warily once he’s out in the hallway. 

“What did Mr. Medina want?” She asks, trying to sound casual and innocent. 

Jess shoots her a skeptical look. “How much of it did you hear?”

She blushes “Pretty much the whole thing.”

Jess shakes his head amusedly. “Why am I not surprised?”

“So, you’re doing better.”

Jess shrugs. “I guess. It’s no biggie.”

“No, it is,” Rory insists. “Even if you don’t want to go to college, this is important. I  _ knew  _ you could do well in class if you tried, and look at where you are.”

“It’s only one ‘A.’”

“Oh, stop being so humble. And self deprecating, jeez.”

“Hey, kettle? It’s pot. You’re-”

“Okay!” Rory exclaims with a laugh. “I  _ get  _ it.”

“What makes you care so much?” Jess asks suddenly.

Rory blinks at him a couple times before smiling softly. “Well, I...you’re my best friend, Jess.”

Something in Jess’ expressions shifts drastically as he smiles, a hint of sadness in his eyes that Rory doesn’t know the root of. “Oh, yeah?”

“Yeah.”

“Besides your mom, of course.”

Rory rolls her eyes. “Fine. Beside my mom. But, still, Jess, you’re…” She trails off, unsure how to put what Jess means to her into words. 

He nods. “I get it. You’re...you’re my best friend, too. My only friend, really.”

She grins unabashedly. “Hey. Promise me one thing.”

He raises an eyebrow. “Yeah?”

She thinks about Dean, how she has no friendship to fall back on with him, and Tristan, who could never be a friend or a boyfriend or anything of the sort. She thinks about the fragility of her relationship with Paris and the solidity of her friendship with Lane, but how still neither of them are quite like what she has with Jess. 

“That no matter what, you’ll stay my friend.”

Jess smiles. “I promise.”

“And promise that you won’t go and fall in love with me.”

Jess looks at her confusedly for a moment before catching on to her impish smile and letting out a laugh. “Well, you only said to promise you one thing.”

She nudges him in the side. “I know. Come on, walk me to my next class.”


	11. Hard Times

**Summary for the Chapter:**

> Rory worries about hurting Jess' feelings. Luke has family issues.

**Notes for the Chapter:**

> This is more of a filler chapter than anything, but there's some important things in it. Hope you enjoy!

“God, I cannot believe this!”

“Okay, what is  _ up _ with you?” Jess demands as Rory plops down on the bench, scowling. “You’ve been in a mood all day. What happened?”

“It’s Dean,” Rory mutters, dragging her foot back against the concrete.

“What? Did he break up with you because you rant and rave at bus stops?”

Rory glares at him. “Ha ha, you’re  _ hilarious.” _

Jess takes a seat next to her. “So? What is it?”

“You know  _ The Donna Reed Show?” _

“Is that one of the ones about the middle class housewife in, what, the fifties or something?”

Rory nods. “Straight out of  _ Pleasantville.” _

“And what  _ did _ Donna Reed do to incur this wrath of yours?” 

“It wasn’t Donna Reed. It was Dean.”   
“Ah, right. What did the boyfriend do?”

“He said he liked the idea of having a housewife,” Rory harrumphs. “And quit calling him that. He has a name, you know.”

“And what was it again?”

Rory shoots him a look. “Okay, bye.”   
“Alright, alright,” Jess concedes. “He said he liked the idea of having a housewife, then?”

Rory nods. “Yeah, he was watching the show with me and my mom - and the two of us make fun of it, of course, but he thought it was  _ nice.” _

Jess snorts. “Caveman.”

_ “Jess.” _

“Aren’t you mad at him?”

“Yes, but…” Rory huffs. “It’s probably stupid. Nevermind.”

Jess cocks his head to one side. “I doubt it. You rarely do anything stupid. Well, except become friends with me.  _ That  _ was pure lunacy.”   
She swats at him. “I’m not the housewife type. I can’t imagine doing nothing all day and just waiting for my husband to come home so I can give him dinner. Is that what he wants? And if it is...do I want to retaliate or do I want to be what he wants? And if I don’t do either, what if he-”

“You are seriously spiraling.”

“Oh, you think?”

“I know you, and I know you wouldn’t be happy being a housewife, especially at sixteen years old. If he can’t handle that, then…”

“I mean, he’s not forcing me to do anything. It still makes me mad, though.”

“Really? I couldn’t tell.”

“You know, if all you’re gonna do is be sarcastic and make jokes, you can stop waiting for the bus with me everyday.”

“But it’s our tradition.”

Rory rolls her eyes. “It’s only been a week, Jess. But  _ anyway,  _ I just don’t know what to do about it. Dean, I mean.”

Jess shrugs. “How big of a deal is it to you?”

“Well, I don’t like it, that’s for sure. But making it into a bigger fight...that wouldn’t be a good idea.”

“Why not?”

“You know, not all of us have the undeniable impulse to cause as much trouble as possible.”

“You’re right, my bad. Go on.”

Rory sighs. “It’s not that big of a deal,” she says, more firmly this time. “And it was probably stupid of me to make it one in the first place.”

Jess listens to her thought journey quietly. “I mean, if it-”

Rory shakes her head and cuts him off. “I’m overreacting.”

Jess frowns. “But-”

“I think I owe him an apology, then,” Rory thinks aloud. “I mean, we all have our dreams, unrealistic or not, right? And I guess they’re not all totally unreasonable.”

Jess snorts. “I wouldn’t count on that,” he mutters to himself.

Rory doesn’t quite hear him. “Wait. I think I know how to make it up to him.”

“Huh. What is it?”

Rory smiles slyly. “Oh, I am  _ so  _ not telling you.”

Jess laughs. “God, Gilmore, you’re filthy.”

Rory frowns for a second before turning bright red. “Shut up!”

Jess shakes his head, grinning. “You  _ had  _ to have known how that would sound.”

“Oh, my god!”

**

Rory is no cook, but she didn’t do half bad. Peach dresses and hoop skirts still aren’t her scene, but Dean looks happy, so really, mission accomplished, right?

Halfway through dinner, Dean asks her about school. She grins and sits up, eager to share. “It’s going really good. I’m actually starting to get along with that girl I mentioned - you know, Paris. She’s actually talking to me. You know, not rudely.”

Dean nods thoughtfully. “That’s good.”

“Yeah. I mean, she’s still not, like, my  _ best  _ friend. That would be Lane. And Jess.”

Dean’s eyes narrow. “Jess.”

Rory can feel the atmosphere shift abruptly, and she fidgets in her chair, uncomfortable under his gaze. “Yeah, Jess. I’ve told you about him.”

“A little. So, you guys are best friends now?”

“Well, I - I guess, kinda,” Rory says. “We’ve been getting along really well, not to mention he waits for me everyday outside school and sits with me while I wait for the bus. That’s something best friends do, right?”

Dean’s brows draw together. “But I wait for the bus with you in the mornings.”

“Right,” Rory replies slowly, unsure of what he means. “And he does in the afternoons. What-”

Dean scoffs. “You really don’t get it, do you?”

“What do you mean?”

“He likes you.”

Rory’s eyes widen. “Dean, I told you, that’s  _ not  _ true.”

Dean doesn’t seem to hear her. “You don’t like him, do you?”   
“Not at all. I like  _ you,  _ Dean, you’re my _ boyfriend. _ Jess is just-”

“A friend, I know,” Dean says, cutting her off, but he doesn’t sound all that convinced. “You don’t think it’s just a little weird that your  _ friend _ does the same thing with you that your boyfriend does?”

Rory blinks at him, stunned. “I don’t - no, Dean I - he’s just - I don’t-” 

Dean just shakes his head. “Whatever. Forget I asked.”

Rory’s heart skips a beat, more from panic than anything else. “Please don’t be mad.”

Dean gives her a smile. “I’m not mad.”

“You promise?” She asks anxiously. 

“Promise.”

“Okay. Good. ‘Cause Jess is my friend, and it means a lot to me that you’re okay with it. And you are okay with it, right?” She asks as an afterthought. 

“Yeah. It’s...fine.”

“Good,” Rory breathes with a smile. “I’m glad.”

She still feels uncertain that it really is  _ fine,  _ but then Dean smiles and she lets herself forget, if just for the rest of the night.

**

But then, after the dinner, when she’s taking off the hoop skirt, Rory realizes that she didn’t have nearly as much fun as she does when she’s with Jess. 

**

“Jess?”

He looks over from his book. “Yeah?”

Rory bounces her leg anxiously. “You know how you’ve been waiting for the bus with me after school everyday?”

Jess smiles softly. “Yeah.”

She takes a breath. “I, uh...you don’t have to - you don’t need to do that anymore.”

Jess’ face falls a little. “Oh.”

“Yeah, I just…” Rory goes to brush her hair back behind her ear, but realizes that she’s wearing a headband. “I mean, that’s a good time to try to get an early start on homework, right? And you - you probably shouldn’t get home too late, anyway, so your stepdad doesn’t get mad, right?”

Jess frowns at her admittedly thin logic. “It takes, like, ten extra minutes to wait.”

“I’m just trying to save you the trouble,” Rory adds hurriedly, unable to ignore how wrong she feels doing this. “It’s unfair of me to ask you to do it.”

“It’s not, Rory, I actually-”

“Jess,” she says, her voice nearly a whisper,  _ “please.” _

Jess’ jaw is clenched as he sits there in silence. “Okay,” he finally says. “I won’t wait for the bus with you anymore.”

She nods, unsure of what else to say. She’s saved from having to worry when he goes back to his book, so she continues to eat, wondering if she did the right thing. Dean obviously didn’t like that Jess would wait with her, and she needs to be a good girlfriend, so she did, right? But then she looks at Jess out of the corner of her eye, and her heart sinks. 

She can’t quite swallow her pride, though, so she just continues to eat, scared to think he might not still wait for her in the morning. Maybe this is a line she can’t uncross.

**

(She doesn’t have to worry, it turns out. He’s waiting for her outside the school the very next day, reading  _ Ulysses.) _

**

Lorelai and Rory go to Luke’s for breakfast every morning, and it’s usually the same every day. They pick a table (which Kirk tries to usurp), Luke chastises them for their orders but ultimately gives them a little bit extra, and they drink multiple cups of coffee to combat the fatigue that accompanies being awake at seven in the morning.

This morning is a little bit different, though - Caesar took their order and served, and there’s been no sign of Luke. 

Lorelai takes a sip from her second cup of coffee before setting it down and looking at Rory, eyes narrowed. “Okay. Speak. What is it?”

Rory looks up from her pancakes in surprise. “What do you mean, ‘what is it?’”

“You’ve got your guilty face on. What did you do? Did you have another meltdown in class again or something, because I don’t know if I can get Dr. Oz on the phone on such short notice.”

Rory sighs. “It’s about Jess.”

Lorelai grimaces. “Oh, friend issues. Yikes.”

“I mentioned Jess when I was having dinner with Dean and I don’t think he appreciated it,” Rory mutters, jabbing at her pancakes. “He  _ really  _ didn’t like that Jess waits for the bus with me after school every day, so a couple days ago I asked Jess...not to.”

“Oh.”

Rory nods, not quite meeting her mom’s eyes. “Yeah. And I thought it was the right thing to do, because it’s important not to hurt Dean’s feelings, but Jess didn’t seem too happy about it. He looked...hurt.”

Lorelai bites her lip. “That’s a tough one.”

“Yeah. I wanted to unsay it, but…”

Lorelai hesitates. “Did Dean ask you to…”

Rory shakes her head. “No, no, I just...I thought it was best. I don’t know. Jess still waits for me before school, so. Maybe it’s not that big of a deal.”

“Maybe not.” Lorelai takes another sip of her coffee. “God, this really isn’t the same when Luke doesn’t make it.”   
“No, it is not.”

They eat in silence for a few minutes, but Lorelai’s got on her  _ I want to say something  _ face, so Rory sets her mug down. “Okay, just say it.”

“Oh, I don’t have anything to say. I never do.”

Rory gives her a look. 

Lorelai sighs. “Okay. Honey, I’m just...if Dean was really that jealous…”

“What?”

“Are you sure that everything’s...good?”

“Yes,” Rory says, a little defensively. “Everything’s good. Everything’s great, actually.”

Lorelai nods slowly “Okay. I just wanted to check.”

“Why do you keep asking me that?” Rory demands. Lorelai is about to answer when the diner door swings open and Luke walks in, slamming it behind him.

Lorelai looks over at Rory with wide eyes.  _ What is up with him? _ She mouths.

Rory shrugs.  _ No clue. _

She glances over at Luke, who is taking Miss Patty’s order, looking way more grouchy than usual. After giving the order to Caesar, Lorelai waves Luke over. “Luke. Luke!”

He sighs heavily and walks over to their table. “What is it, Lorelai?”

“Oof, someone’s grumpy!”

Luke gives her a flat look. “I think I have the right to express my emotions however I want to in my own diner.”

“Did something happen?” Rory asks.

Luke glances over at his truck. “Family problems,” he says gruffly. “Can I get you two anything? More coffee? A sedative?”

“Kirk said he got some horse tranquilizers. Do you have any of those?” Lorelai asks, trying (and more or less failing) to keep a straight face.

Luke rolls his eyes. “Rory, you done?”

“Yep,” Rory says, swallowing her last bite of pancake. 

“I can take that plate off your hands.”

Rory smiles gratefully and goes to hand it to Luke, but it slips out of her hands and falls onto the floor, breaking into several pieces.

Rory’s heart drops. “Oh, my god, Luke, I am so sorry.” She goes to start picking up the pieces, but Luke shakes his head and beats her to it.

“It’s okay. It happens.”

Rory swallows, staring down at the shards of the plate in dismay. “I’m really sorry. I didn’t mean to - it was an accident - it just slipped, and-”

“Rory.” Luke gives her a gentle smile. “It’s okay.”

Rory nods and sinks back into her seat, feeling like she wants to cry. Lorelai gives her a worried look, but she doesn’t say anything.

(Luke gives her a danish on the house before she goes, which makes her feel a little bit better, but not any less guilty.)

**

When Rory gets to school, there’s no sign of Jess. Her heart drops, her immediate thought being that maybe he really  _ wasn’t  _ okay with what she asked of him and he’s done with her, forever. She waits for him for a few extra minutes, but when it’s five minutes to the first bell and he still hasn’t shown up, she walks inside and heads for class.

**

By the end of first period, Jess still isn’t there. And yes, Rory knows he’s more of a slacker than not when it comes to school, even if he’s been doing a little bit better lately, but it’s never been like him to actually  _ skip.  _ So when he isn’t there at lunch, and he doesn’t show up for the rest of the day, Rory worries. She tries to call him, but his phone goes to voicemail.

There’s a feeling of dread in her stomach the entire way home.

**

“So, he didn’t even show up?”

“Nope. He wasn’t in any of his classes all day.”

“And he’s never skipped before?”

Rory shakes her head. 

Lorelai frowns. “God, that’s weird. Well, I hope he shows up Monday.”

Rory nods. “Me, too.”

Their conversation is cut short when a motorcycle pulls up. Rory watches in curiosity as the man takes off his helmet and then - and then it’s her  _ dad,  _ and everything is absolutely good.

**

After the more or less disastrous dinner with her father’s parents  _ and  _ Emily and Richard, Rory just wants to hide away in her bed for the rest of the weekend. However, her phone rings, and she leaps to answer it, hoping that it’s Jess.

“Hello?”

_ “Hey, Mary.” _

Rory’s stomach drops. “How did you get my number?”

_ “I don’t think that’s especially important. Let’s just say that I have...connections.” _

“Tristan, please do me a favor and never call me again. Ever.”

He laughs.  _ “C’mon, Mary.” _

“It’s Rory.”

_ “Look. I like you, you like me-” _

“Are you crazy?”

_ “I can read between the lines. I’m not stupid, remember?” _

“Well, get some reading glasses, because you didn’t do a very good job.”

He laughs again, making her grimace.  _ “Now that I’ve gone through all the trouble to get your number, how about you repay me by going on a date with me?” _

“You cannot be serious!” Rory exclaims.

_ “Don’t tell me you’re still with that farmboy.” _

“His name is  _ Dean,”  _ Rory hisses, “and yes, I’m still with him. So how about you leave me alone?”

_ “Mary-” _

Politeness be damned, Rory hangs up and lets her phone drop onto the comforter. Today has been absolute  _ hell,  _ and all she wants to do is talk to her best friend.

She tries calling him again, but there’s no answer at all. 


	12. Persuasion

**Summary for the Chapter:**

> Rory confronts Jess about his absence on Friday. Later, she faces a difficult decision between her mother and the boy she's dating.

**Notes for the Chapter:**

> Hey! I'm very glad I was able to write this and post 2 days after the last update while actually liking this chapter. I think it's pretty cute and (hopefully) in character, so I hope you all enjoy it too!  
> NOTE: I guess there are kind of some spoilers for Dawson's Creek season four if you haven't watched it, but I only talk about the episode "Future Tense" (4x04). That aired on October 25th, 2000, which might give you an idea of how far into the school year they are. But also don't dwell on it too much, I'm sure I've included more weeks than there would have been between this and Rory's birthday in chapter five.

Christopher leaves. Of course he does. That’s what he does, he _leaves_ \- well, admittedly, it’s not like he was ever there in the first place, really, but he’s gone now. He leaves with a promise to see them again soon and a bunch of baggage that Rory can’t get herself to begin to unpack. 

Lorelai insists she’s fine, but Rory isn’t oblivious, she _knows_ something happened between them (and she’s not naive, either, she has a pretty solid guess as to what), and, besides, she knows her mother. Lorelai may put on a brave face for her daughter, but Rory can see the facade starting to fall apart.

Regardless, she still has school, and dwelling on her father’s visit for any longer is sure to drive her crazy. Rory loves her dad (how could she not?), but at the end of the day, she’s got tests to take and papers to write and he just needs to stay a footnote for now.

**

“Hey, Rory?”

Rory finishes tying her shoe and looks up at her mom. “Yeah?”

Lorelai takes a sip from her coffee. “Have you heard from Jess?” She asks hesitantly. 

“No,” Rory admits. “I tried calling Friday night, but he wasn’t picking up, so I didn’t try again.”

Lorelai nods thoughtfully. “Hope he’s at school today,” she supplies with a sympathetic smile.

Rory lets out a small breath. “Me, too.”

Their morning routine is smooth, even with Lorelai taking the clip out of Rory’s hair on her way back from the toaster. (“The clip is better without the sweater, trust me.”) They move around the kitchen in contented silence before Lorelai speaks up again. 

“So, I did a little digging on Luke’s _mood_ Friday morning,” she mentions casually, mouth full of pop-tart.

“Say it, don’t spray it,” Rory scolds. “And by digging, you mean nagging on him until he tells you, right?”

“Well, yeah, duh.”

‘Just confirming. What did you find out?”

Lorelai sets her mug down on the counter. “Well, he was _really_ adverse to telling me, but I got a little out of him. Turns out, he’s got a nephew in Hartford.”

“Huh. He’s never mentioned that before.”

“I know, right?” Lorelai shakes her head. “Luke is a man of mystery.”

“We’ve known that for a while, though.”

“True, true.”

“Did he say anything about his nephew?” Rory asks curiously.

A sly smile spreads across Lorelai’s face. “Oh, I managed to pry some information out of him. Which, mind you, is one of the hardest things I’ve ever done. And giving birth to you, my dear, was _not_ a walk in the park.”

Rory scrunches up her face at her mom. “Yeah, yeah. Now tell me.”

“So, he’s got this nephew, right? Turns out his sister - Luke’s sister - married some super rich guy - like, Daddy Warbucks rich - in Hartford. And, like, one month after that, his sister has to go to rehab.”

“Wow.”  
“There’s more,” Lorelai gushes, eyes alight. “So his nephew is stuck with his step-family, right - although I do get the feeling that his mother probably wasn’t much comfort if she had to go to rehab, but I digress. I guess tensions just run really high, and his nephew’s a bit of a rule breaker, so every now and then Luke has to drive over there to do damage control.”

“Wow,” Rory breathes. “That’s a lot more than I was expecting.”

“Right?” 

“Is his sister still in rehab?”

Lorelai shrugs. “Dunno. He wouldn’t tell me anything else about her.”

“Weird.”

“Totally. What’s even weirder, though, is that he just totally clammed up,” Lorelai continues. “Like, I tried to ask more about his sister, and he almost kicked me out. Physically. Luckily, I reminded him that I am a lady, so I think he came to his senses.”

Rory grimaces. “So there’s something not so good going on with Luke’s sister.”

“That’s what I was thinking. Now, I’ve been theorizing - I’m thinking mainly rehab or maybe prison, but honestly, I’m not really sure. Maybe she’s one of those trophy wives who get killed by their husbands for the insurance money or something.”

Rory stares down at her shoes. “That must be really hard on Luke.”

Lorelai forces a smile. “Ah, he’s Luke. If anyone can handle a mess, it’s him, right?”

“Fair point. He does have to deal with you every day.”

“True.” It takes Lorelai a moment, and then she exclaims, “Hey!”

Rory scampers out of her chair. “I gotta go!”

“Come back here, missy!”

“Bye!”

**

The whole bus ride to Hartford, Rory is apprehensive. She has no idea if Jess will be at school or not, and even if he is, she has to admit, she’s a little upset with him. He ghosts for a day and doesn’t even return her calls. _(We’re supposed to be best friends,_ she thinks, a little bitterly.)

But then she steps into the courtyard, and there he is, leaning up against the brick wall, his tie and collar loose and his sleeves rolled up as always, causing her heart to skip a beat. He’s reading _On The Road_ (a re-read, she’s sure) and holding it from the top in that weird way that she always gives him grief for. 

“Jess.”

He looks up and smiles when he sees who it is, slipping his book into his back pocket and leaning back up against the wall. “Hey, Gilmore.”

“Don’t ‘hey, Gilmore’ me,” Rory says in a hushed voice. “Jess, where were you on Friday?”

Jess’ jaw ticks. “Ah, no beating around the bush, then.”

“Of course there’s no beating around the bush! You didn’t even tell me.”

“It was an unplanned absence,” Jess says casually. “Nothing to, you know, write home about or anything.”

_“Bullshit.”_

He raises an eyebrow. “Is that a word you only save for me?”

“You didn’t answer my calls.”

He shrugs. “I was busy.”

“With what?” Rory demands. 

Jess smirks. “You know, I think you’d be really good on _Law and Order.”_

“I show up, and you’re not here - and I waited, too, and you just _weren’t there-”_

“I think you could top Orbach’s witty one-liners no problem.”

“And then I kept an eye out all day - I had to eat alone at lunch, too-”

“You’ve really got down the whole-”

“Jess!” She exclaims. His eyes widen and he shuts up immediately. “Take this seriously for one second, please.”

Jess glances away from her for a moment. “Rory, it really wasn’t that big of a deal,” he finally says after a long pause. “Just some family stuff, okay?”

“And you’re okay?” 

He offers her a half-smile. “I’m fine.”

“Okay,” she breathes out, nodding, anxiously pulling her sweater over her hands.

Jess glances down at what she’s doing. “I really had you worried there, huh?”

She doesn’t reply.

He lets out a sigh. “Sorry,” he offers with a half-shrug.

“It’s just…” She swallows. “I really wanted you there, Jess.”

He frowns in concern. “Did something happen?”

Rory leans up against the wall beside him, staring at the ground. “My dad came to visit.”

“Ah, the father.” Jess grimaces. “That’s always a doozy.”

“I mean, it was fine at first - I don’t always get to see him, and he _never_ comes to Stars Hollow, so this was just...really nice. But then, his parents came to Friday night dinner, and it was just...a mess.”

“Let me guess. They’re still not thrilled that the prodigal son knocked up a woman and didn’t marry her?”

Rory nods. “I’m just a mistake to them, you know? And I know - I know that that’s not how he sees me, or my mom or her parents or-” She cuts herself off.

“It still kinda stings,” he supplies.

She nods. “Yeah. It does.”

Jess exhales slowly before replying. “Sorry I wasn’t there.”

“There’s more,” she adds miserably.

Jess winces. “Oh, jeez.”

“Tristan called me, too.”

“What?”

“Oh, yeah, he just called me right up, and I have _no_ idea how he got my number, but I’m not really sure that I want to know. He _asked me out._ Can you believe that?”

Jess scoffs. “Unfortunately, I can.”

“I mean, has he ever heard of _consent?”_

“Apparently not.” Jess shakes his head. “And he didn’t say anything about how he got your number.”

“Nope.”

“Fucking asshole,” Jess mutters. 

“Yep.”

They stand in silence for a moment. “I just got into some trouble with my step-father,” Jess says suddenly.

Rory whips her head to look at him. “What?”

“He doesn’t really appreciate jokes.”

“Why, what did you do?”

Jess smirks.

“Jess? What did you do?”

“Is everything good now?” He asks, ignoring her question. “With your dad and your mom and...well, you.” 

“I guess. I think he slept with my mom, though, so I guess that happened.”

Jess makes a face. “Those words don’t sound natural coming out of your mouth at all.”

Rory glares at him. “If you start calling me _Mary,_ I’m going to have to kill you.”  
He laughs. “Come here, Gilmore,” he says after a moment, wrapping an arm around her and pulling her against his side. She rests her head on his shoulder, breathing in his familiar scent and in that moment, she knows she’s forgiven him. 

“I _am_ sorry,” he murmurs. “That I wasn’t there when you needed me.”

She glances up at him, eyes soft. “Jess, I’m always going to need you.”

He looks down at her with a grin. “Oh, yeah?”

She returns the smile. “Yeah.”

“Good,” he breathes out. “Good.”

**

Paris corners her in the hallway after class. Now, Rory likes to think that she’s got the whole Paris Geller thing down, understood, memorized, but Paris keeps finding new ways to catch her off guard. 

“Hey. Rory.”

Rory blinks in surprise. “Me?”

“That _is_ your name, isn’t it?”

“Yeah…”

“Can we talk for a second?”

Rory glances over at Jess, who is looking at her expectantly. “I guess, yeah.”

“God, could you reply any slower? Stop making googly-eyes at Mariano and listen.”

Rory’s face heats up. “I am _not-”_

“I don’t want to hear whatever lame excuses you’ve got locked and loaded.”

“You’re the one dragging this out, Paris.”  
Paris huffs. _“God._ Look, we’ve got that stupid test from Medina in a few days, and I was just wondering if you wanted to study with me, okay? But now I’m starting to doubt your mental capability, so answer quickly before I change my mind.”

Rory’s eyes widen. “You want to study with me?”

“I wouldn’t say _want,_ but you are the next best student in the class, so I figured, what’s the harm?”

“Thanks. I think,” Rory replies, frowning. “Sure, I guess. When did you have in mind?”

“I don’t know, today after school?”

“Okay,” Rory replies, still surprised that this is happening. “We can meet in the library?”

Paris scoffs. “Working in the school library? Please. Why not just study in an alley, or in Chernobyl for God’s sake.”

“Paris, do you have something against the Chilton library?” Jess suddenly asks, inserting himself into the conversation.

Paris rolls her eyes at his over-concerned tone. “Look, I get that Chilton is as fancy as it gets, but they’re cheap here, too. There’s probably asbestos in the ceilings or something. Silent killers, you know.”

Jess starts to laugh, but he covers it with a cough. Paris gives him a look before turning back to Rory. “We can go to the Hartford Public Library. Just meet me outside in the courtyard after school, and I can drive us over there,” she says before she starts to walk away. 

“Oh, please can’t I come?” Jess calls after her, but Paris ignores him. “Rude,” he says, shaking his head. “Not even inviting me? That’s just cold.”

Rory gives him a look. “This could actually be good, Jess. I mean, she asked me to work with her. This is the same Paris that wanted to rip my head off a couple weeks ago.”

“A Bangles concert really does wonders for a relationship, huh?”

“I guess so,” Rory says with a smile. “You know you don’t have to egg her on like that, though - or, you just shouldn’t. She might actually kill you.”

Jess snorts. “I wouldn’t count on it. Geller and I? We’ve got a strange sort of kinship.”

Now it’s Rory’s turn to laugh. “You and Paris? I’ll believe it when I see it.”

“And see it you will.”

“Is that a promise?”

“I don’t make promises,” Jess says with a mischievous grin. “I only ever break them - on principle, of course.”

Rory rolls her eyes. “I can’t stand you.”

“Don’t worry. You’ll have a newfound appreciation for me after studying with Paris Geller.”

“I thought you said you two have a kinship.”

“I said that? Really? And you took me seriously?” He shakes his head. “God, Gilmore, I really don’t know if you’re cut out for this school after all.”

She smacks him in the chest. 

**

“How many poems did Emily Dickinson publish while she was alive?”

“Seven. But overall she wrote at least one thousand, seven hundred seventy five.”

“Correct. What was different about her poetry?”

“Uh, most of her poems were about harsh subjects, but she also showed an optimistic understanding about emotional pain, strife, death, nature, and love.”

“Good.” Paris sets down the flashcards. “Okay, we’ve finished all of these. I think we’re done here, don’t you?”

“You know, this wasn’t so bad,” Rory muses, closing her notebook.

“What do you mean?”

“Well, I wasn’t sure if after the concert we’d actually hang out again. But this was pretty nice.”

Paris gives her a half-shrug, trying not to give away any emotion. “Could’ve been worse.”

“That’s the spirit.” 

Paris rolls her eyes, but she’s starting to smile. “I wouldn’t get too excited.”

“From you, it’s a glowing compliment.”

“Whatever.” She hesitates for a moment. “What’s the deal with you and Mariano?”

Rory’s head snaps up. “What?”

“You and Mariano.”

“We’re just friends,” Rory says, and _wow,_ is she tired of repeating that. “I’m still dating Dean. Why? Do you…?” She trails off, her curiosity still getting the better of her. 

Paris’ eyes narrow. “What, you think I have crushes on all the guys now just because I _asked?_ I swear to god, Gilmore, I’m-”

“Okay, okay, god. Sorry.”

Paris sighs. “It’s...fine. I was just wondering. You two seem really close.”

“I mean, we are. But he’s-”

“A friend. You’ve mentioned.”

“Do people still think I’m dating him?” She asks anxiously. 

“Not really,” Paris says. “I mean, after the whole showdown at the formal I think everyone understands you’re with Frankenstein.”

“Frankenstein?”

“Frankenstein’s monster, whatever, my bad. Didn’t peg you for one of those.”

“No, I meant - I got what you meant. But...what did you mean?”

Paris rolls her eyes. “Tall, a little scary, anger issues. Sound familiar?”

“Hey, Dean does not have _anger issues.”_

Paris shoves her notebook in her bag, seemingly unbothered. “Okay.” 

“He _doesn’t.”_

“I heard you, jeez.”

Rory glances over at Paris, and, catching the look on the other girl’s face, she groans. “I can tell you have something on your mind, so just say it.”

“I get that you’re not dating Mariano, but…” Paris hesitates. “You do have a thing for him, don’t you?”

Rory can feel her face heating up. “What? I don’t - I couldn’t - he’s my - and he, he’s _Jess -_ I’m dating Dean,” she finishes weakly, aware that she did not sound convincing in the slightest.

“Very convincing, Gilmore.”

“I don’t have a - a _thing_ for Jess.”

“Okay, maybe not a _thing,”_ Paris says with a shrug. “A crush?”

Rory gives her a look. _“No.”_

“Could’ve fooled me. You should take it down a notch, though, with all the denial. One might start to think you’re not telling the truth.”

“I’m not-”

“Well, _I_ know you’re not lying - believe me,” Paris adds with an exasperated tone, “but other people might. And it doesn’t help that he’s always looking over at you with those big sad eyes of his. It’s enough to fuel a whole new season of _Dawson’s Creek.”_

Rory glares at her. “You can leave now.”

“Hey, I’m just pointing out the obvious.”

“It’s not obvious because it’s not true,” Rory insists. “Jess doesn’t have feelings for me, and I don’t have feelings for him. So can we drop this? I get enough of this from Dean,” Rory adds to herself in a low voice. 

Paris scrutinizes her for a minute before relenting. “Alright. Thanks for studying with me, by the way.”

Rory smiles. “Yeah, no problem.”

“I’ll...see you tomorrow, I guess.”

“Sounds like a plan.”

Paris rolls her eyes at that - albeit with a smile.

**

Wednesday night is _Dawson’s Creek_ night, which means Lorelai and Rory always go all out. Lorelai ordered pizza and Rory made popcorn, which means they’ll both _definitely_ feel sick by the end of the night. It’s a tradition, after all.  
“Okay, ten minutes to go,” Lorelai announces excitedly. “Theories?”

Rory hesitates. “Well, the promo showed that Joey’s gonna get drunk and that Jen might do drugs with Drue. So...I’m guessing that both of those things will happen.”

“You’re no fun,” Lorelai pouts. “And, besides, I trust Jen. I don’t think she’ll do that.”

“You said that right before Andie cheated on the PSAT,” Rory reminds her mom. 

“Yes, but this is _Jen_ we’re talking about.”

“Maybe Joey and Pacey won’t fight,” Rory suggests sarcastically. “That would be a first. They were so _good_ last season, but now all they do is fight.”

“She’s gonna go back to Dawson eventually. Might as well rip off the band-aid.”

“Take that back!”

Before Lorelai can throw a pillow in return, the phone suddenly rings. Rory takes the chance and leaps up to answer it. 

“Hello?” 

_“Hey.”_

Rory grins. “Hey, yourself.”

 _“I, uh, I was wondering if you had any plans tonight. They’re showing Pulp Fiction at the movie theater and you have_ got _to see it. I still can’t believe you haven’t yet.”_

“Oh, uh…” Rory winces. “Well, I’m watching _Dawson’s Creek_ with my mom tonight.”

_“You can always record it, right?”_

“I don’t know...I guess we can, but we look forward to it every week.”

Dean sighs. _“Just tonight. Please?”_

“Dean…”

_“Pretty please? With sugar on top?”_

“On top of what?”

_“On top of the many powdered donuts I will buy for you if you go see the movie with me tonight.”_

Rory glances over at her mom. She knows Dean isn’t going to stop asking until she agrees to go, so she reluctantly relents. “...Okay. I guess the show can wait.”

_“I’ll pick you up in a few.”_

“Sounds like a plan.”

Rory hangs up and blows out some air. This doesn’t really feel right, and she _knows_ it’s not what she wants, but all relationships need compromises to last, right? Although something is telling her that this isn’t really a compromise at all. 

She glances over at her mom. “Mom, can you, uh, let me off the hook for the night? Dean wants to see _Pulp Fiction_ with me.”

Lorelai frowns. “But we’ve been waiting for this for a week.”

“I know, but it’s really important to him.”

“And this is important to us.”

Rory bites her lip. “I kinda already told him I would go,” she admits, feeling oh-so guilty.

Lorelai purses her lips together, staying silent for a moment. “I guess I can record it,” she says with a sigh. “But it won’t be the same.”

“Thank you,” Rory says apologetically. “I’m sorry. This is a one-time thing, I promise.”

Lorelai nods, but Rory can’t help but think that she looks unsure. 

And, honestly? So is she. 

**Notes for the Chapter:**

> [Insert "could a depressed person make THIS" ben wyatt meme]


	13. Everything is Illuminated

**Summary for the Chapter:**

> Chilton hosts a winter carnival.

**Notes for the Chapter:**

> TIMELINE UPDATE: Don't pay too much attention to the timeline - it's very messy and does not make sense. Just assume that this is a couple weeks after the last chapter, so like mid November.  
> This is probably one of my favorite chapters so far, so I'm excited to hear what you think!

“So, grandpa, how was your trip to Rome?” 

Richard smiles at his granddaughter. “It went very well, I don’t mind telling you. Thank you for asking, Rory.”

“Of course. Rome seems really nice - I’d love to go there someday.”

“Well, maybe you and your mother will go there on your trip to Europe.”

Rory grins. “I hope so.”

“Yeah, that could be fun,” Lorelai agrees. “You, me, and a million _smoking_ hot Italian men…” She sighs wistfully. “Now that’s an image I shan’t soon forget.”  
“Really, Lorelai, do you have to do this every time your father takes a trip?” Emily scolds. “First it’s English men, then French men, et cetera. What’s next? Do you have a thing for Czechoslovakian men, too?”

“Mom, czech - czech...czechoslaba - czechoslov - _whatever_ it’s called dissolved in the nineties.”

 _“Really?_ Well, since you’re suddenly our resident history scholar-”

“Did you have time to do anything other than work?” Rory asks her grandfather, cutting off her grandmother. She’d love to avoid yet another argument between her mom and Emily, especially after what happened the last time. 

“Unfortunately not,” Richard answers. “Business is booming over there, which is fantastic for the company, but doesn’t leave much time for personal excursions.”

“Well, maybe next time, right?”

Richard nods. “Next time. And I’ll bring you back something, too - whatever you’d like.”

“Does that include the men?” Lorelai asks. 

“So, Richard,” Emily says pointedly, “don’t we have something we need to talk to the girls about?”  
“Do we?” Richard asks, confused.

“Yes, we do.”

Richard hesitates for a moment. “Oh, oh, yes. Yes, we do.”

Lorelai frowns and looks between her parents. “Is one of you dying or something? Is it time for more post-it claiming? I’ve had my eyes on that table in the foyer for a couple weeks now.”

Emily rolls her eyes. “I’m not dignifying _that_ with a response.”

“A-ha! You just did.”

“Emily and I have to, uh, cancel next week’s Friday night dinner,” Richard explains. “We have to attend another dinner party that night. It’s very important for my company, and it cannot be postponed.”

Lorelai’s jaw drops. “Are you kidding? When I tried to postpone for Rory’s birthday party, you said-”

“We don’t see them very much,” Emily says sternly, “and we already postponed once after your father had to go to the hospital-”

“The Huntzbergers are very good friends of ours,” Richard informs Rory and Lorelai calmly. “Why, I’ve been in business with Mitchum Huntzberger for years.”

“He has a son a year older than Rory,” Emily adds excitedly. “Maybe someday you’ll meet him. Actually, now that I think of it, you could get along with him really well. They would make such a sweet couple, wouldn’t they, Richard?”

“Hey, before you start pimping out my daughter-”

“Hey!” Rory objects.

“-maybe take a second to remember that she _has_ a boyfriend,” Lorelai continues. 

Emily purses her lips together. “Oh. You’re still with - what’s his name?”

“Dean,” Rory reminds her.

“Ah, right. The bag boy at the market.”

“Yes, I’m still with him.”

“You haven’t met any boys at Chilton?” Richard asks, sounding surprised. “I’m sure you could find someone there who matches your intellect with no problem.”

“I’m still dating Dean.”

“What about that boy? Jess?” Emily asks. 

“A hot Italian man of your own,” Lorelai adds, not so helpfully.

Rory shoots a look at her mom. “Did anyone hear me say that I’m still dating Dean?”

“Fine, fine.” Lorelai sighs. “Let’s stop trying to set Rory up, now, shall we?”

“Thank you. And postponing the dinner actually works out for me,” Rory says. “Chilton’s hosting a winter carnival next Friday, so I can go to that instead.”

“And leave me home alone?” Lorelai pouts.

“Hey, you can always annoy Luke instead.”

“A very good point.”

Emily looks at Richard, exasperated. “Can you ever track a single thing these girls say?”

“Not often,” Richard says, “but isn’t that part of the fun?”

Rory grins and goes back to her food. He’s definitely got a point. 

**

“Jess?”

Jess looks up from his book and sets it down on the table. “Yes, ma’am?”

“Were you planning to go to the carnival on Friday?”

“Probably not,” he says with a shrug. “Were you?”

“I don’t know, I mean, my grandparents canceled our dinner, so I figured, why not?” She replies, pushing her food around with her fork. “It’s a nice idea, but I don’t want to go alone,” she adds pointedly.

Jess lets out a deep sigh. “Rory…”

“Look, I know these things aren’t your scene, but you showed up to the dance, didn’t you?”

Jess grimaces. “That was...an impulse decision.”

“Why won’t you go?” When he doesn’t answer, she grins triumphantly. “See, you have no good reason not to go.”

“Yes, but I don’t have a reason to go, either,” he points out.

Rory gives him an unimpressed look.

“Fine. One reason.” He lets out an exasperated sigh. “Stop giving me that face.”

She bats her eyelashes. “Please?”

“No.”

“Want to find out if I can make myself cry?”

Jess groans. “You’re never going to make this easy on me, are you?”

“Well, I could, but what would be the fun in that?”

He gives her a look. “I’ll hate every second of it.”

“You’re a big boy, you can handle it.”  
“It’ll be cold.”

“You have a coat.”

“I suck at all those games.”

“Consider it practice.”

She holds his steady gaze and keeps a straight face. After a moment, he just sighs deeply. “You owe me big time. Bigger than ever, you hear me?”

“Yes! Thank you, thank you, thank you!” She grins and hugs him. “You won’t regret it.”

“No?” He says, eyeing her warily.

“No,” she confirms. “I have never once had a bad carnival experience, so you’re in good hands.”

“Yeah, but you literally live in the town from _Pleasantville,”_ he says flatly. “In the _beginning_ of the movie. Now let go of me,” he adds, shaking her off.

Rory smiles at him brightly, to which Jess rolls his eyes. 

“At least let me bring a book.”

“What, did you think I was going to share?”

He shakes his head. “You’re impossible.”

“It’s part of my charm.”

Jess hesitates, then smiles. “Yeah, it is.”

There’s something so warm in his eyes that his stare causes Rory’s breath to hitch, and she looks away quickly to ease the tension. 

“I’ll pick you up, then? At six-thirty?”

Rory whips her head up (she’s gonna get whiplash one of these days if he keeps surprising her) and stares at him in surprise. “What?”

“Why not?” Jess says with a noncommittal shrug - but the tips of his ears have turned pink. “I mean, you’re forcing me to go, so might as well, right?”

“Very considerate of you.”

“Well, you know me. Mr. Considerate.”

“That’s your reputation for sure.”

“Unless you don’t want me to,” he adds. She quite likes him when he’s flustered, she decides. 

Rory gives him a reassuring smile. “Why not, right?”  
Eventually, he smiles back. 

**

The night of the carnival, Lorelai watches her daughter with a knowing gleam in her eye as Rory stares in the mirror for five minutes and ultimately decides to leave her hair down, and as she fusses over which gloves she should wear.

“So, this carnival,” Lorelai starts, handing Rory a mug of coffee. “I’m surprised you’re so excited for it.”

Rory shrugs. “It seems fun.”

“It does.” Lorelai pauses. “So, are you just going by yourself, or are you meeting Paris there, or…”

“No, I'm going with Jess,” Rory says before taking a sip of her coffee. 

For some reason, her mom doesn’t seem surprised. “Jess, huh?”

“Yeah. He’s picking me up soon.”

“He’s picking you up?”

Rory nods. 

“Well, it was very nice of him to offer.”

Rory smiles. “Yeah, it was.”

“Does Dean know about this?” Lorelai asks after a moment of hesitation. “You, going with Jess?”

“He, uh - well, I didn’t - he doesn’t - and the carnival, I didn’t - I didn’t tell him about the carnival,” Rory stammers, a sinking feeling in her stomach. “Why? Are you saying I should be going with Dean and not Jess, ‘cause Jess is my friend, mom, and I have the right to-”

Lorelai holds up a hand. “Rory, breathe, please. I’m not saying you should be going with Dean, I’m just…” She sighs. “There’s gotta at least be a reason that you didn’t tell Dean.”

Rory doesn’t quite meet her mother’s eyes. “It never came up.”

“And he didn’t ask to spend the night with you when he found out our Friday night dinner was postponed?” When Rory doesn’t answer, a realization dawns on Lorelai. “He doesn’t know we don’t have dinner,” she says slowly.

“I tried to tell him, I just-” Rory swallows. “I don’t know. I knew he would insist on doing something, or that he’d want to go, and the last time he went to a Chilton event…” She sighs. “Well, it didn’t go super well.”

“And it has nothing to do with Jess?”

“Why does everyone keep saying stuff like that?” Rory questions. “I’m sick of it! Not everything is about _Jess,_ or even about a guy! It doesn’t all go back to him. I just - I didn’t want-”

“Rory, I’m not saying it’s just about Jess, I just think that-”

“What? What _do_ you think?” Rory demands. “That I have feelings for Jess? That I’m lying to Dean?”

“You are lying to Dean!”

“So what? I want to spend this night with my _friend,_ who, yes, is Jess, but that’s-”

“Rory, can’t you tell that I’m worried about you?” Lorelai yells. “The fact that you need to lie to your boyfriend so you can have a night without him raises him a million red flags, which, honestly, is just the tip of the-”

“Why are you so afraid of me being with Dean?” Rory shouts back. “He’s nice, and he _likes_ me, mom, he actually likes me - maybe he wants to spend a lot of time with me, but he’s my _boyfriend!”_

“That doesn’t give him the right to _control-”_

“Mom, that’s just how Dean is. He likes to spend a lot with me, and he gets a little jealous, but that’s _natural.”_

“Have you lost your mind? The Rory Gilmore I know - the list maker who analyzes everything - wouldn’t let a guy do this to her!”

“He’s not doing anything to me!”

“You can’t even tell him that you’re going to a carnival with your friends!”

“And I can’t even tell you that without causing a huge fight, so I guess the two of you are even,” Rory spits back.

Lorelai’s eyes narrow. “Watch it, kid. I’ve been around the block a few more times than you, and I _know_ the signs. Just because he’s not hitting you doesn’t mean it’s not unhealthy.”

“I can’t believe this!”

“He’s jealous all the time, gets mad at you a _lot,_ isolates you from your family-”

“Not watching _Dawson’s_ was _my_ choice, mom!” Rory exclaims. “Or is that totally unbelievable because I can’t make my own decisions?”

“That’s not what I’m saying, Rory, you _know_ that’s not what I think.”

“And then it all comes back to Jess somehow, right?” Rory demands. “Gonna use some backwards psychology to prove that me not telling Dean about this means that I’m in love with Jess?”

“Just let me ask you one thing.”

“Fine. What?”

Lorelai purses her lips together as she looks at her daughter. “Why did you spend so much time on your outfit and your hair tonight?”

Rory scoffs. “Are you _serious?”_

“Just answer the question.”

“Is it a crime to want to not look disgusting at a school event?”

“Honey, there’s a pretty big difference between looking disgusting and spending ten minutes fussing over how to do your hair!”

“And that’s your proof.”

“You’re wearing your nice sweater.”

“And jeans!”

“Rory-”

“Stop!”

“Listen to me!”

Rory glares at Lorelai. “Why should I? Do you have some groundbreaking observation that’s going to magically change my mind and make me believe your crazy logic?"

“I think you’re falling for Jess.”

“No!” Rory huffs. “I’m _not_ falling for Jess.”

Lorelai sighs deeply. “It was just a thought, okay? No need to get so bent out of shape over the wonderings of a batty old woman.”

Rory crosses her arms across her chest. “Well, it was wrong.”

“Okay.”

There’s a knock on the door. “That’s Jess,” Rory says flatly, grabbing her coat and gloves. “I have to go.”

“Fine. Be back at eleven.”

“Fine.”

Rory finishes pulling on her gloves right before she opens the door. “Hey, Jess,” she says with a smile. 

He nods in greeting. “Hey. You ready to go?”

“Yep.”

Once they’re in the car, Jess glances over at Rory, hand on the gearshift. “Is everything okay?” He asks, catching her off guard. 

“What do you mean?”

“You look upset. If it’s the dent in the car, I guess we can make a pit stop and get it fixed, but something tells me it’s not that.”

Rory shakes her head and smiles. “I just...I got into a fight with my mom, that’s all.”

Jess grimaces. “Sorry about that.”

“It’s not your fault,” she says, but she admittedly isn’t sure if that’s entirely true.

“Yeah.” He gives her a sympathetic smile. “We’ll have a good time tonight, okay?”

“Wasn’t I the one dragging you to this?”

“Well, I’ll just have to try my hardest to enjoy it.”

She smiles and kisses him on the cheek, surprising him. “Alright. Let’s get going, Argyle.”

He rolls his eyes good-naturedly and starts the car.

**

“Oh, my god,” is all Rory can say when they pull up to the carnival.

Now, she’s no stranger to the fact that Chilton is _rich,_ but she expected it to be along the lines of the Stars Hollow High Winter Carnival, but this is much, much _more._

The white snow blanketing everything and the strings of lights decorating all the booths and rides compliment the darkening navy blue sky perfectly. There’s a ferris wheel, a carousel, games and food and probably even more and oh my _god_ is she glad that she came.

Jess looks at her amusedly as she exclaims excitedly. “Jess, oh, my god,” she breathes, looking around at all the booths. 

“Yeah, these people really go all out, huh?” He says, slowing to a stop and looking up.

Rory nods emphatically. “And I am _so_ glad that they did. Come on, let’s go play some games!” She grabs his hand and starts to drag him towards one of the booths.

“Gilmore, I told you I suck at these. Do you ever listen to me, or is this a selective memory issue?”

“What?”

“Oh, shut up.”

“Just stand there and watch me win,” she suggests. 

“So it’s like that, huh?” Jess says with a laugh. 

Rory grins. “Yep. Let’s do that one,” she decides, pointing towards a booth with some teddy bears on display. Jess groans, but he follows her.

“That’ll be a dollar,” the man running the booth says. Rory begins to reach into her pocket for some cash, but Jess stops her. 

“Allow me.”

“Jess, you don’t have to-”

“I know,” he says. “But I’m still doing it.”

She smiles thankfully and lets him hand the dollar to the man running the booth, who gives her three baseballs.

She misses on the first try (which Jess laughs at a _lot_ more than necessary) but she knocks all three bottles down on her second try. The man hands her a little stuffed bear.

“That thing is _cheap,”_ Jess whispers as they walk away from the booth. “Probably worth about a quarter.”

“Not with taxes. And, sure, it’s dinky, but it’s sweet.”

“And where are you going to put it?”

“We can stock up on prizes and put them in the car.”

Jess rolls his eyes. “I’ll just bring that to the car now,” he says.

“Aw, you’re nice.”

“Watch it.”

“A real gentleman.”

“I _will_ throw it away.”

“And I’ll just win another.”

He rolls his eyes and takes the bear from her. “Just give me a minute.”

Once he’s out of earshot, a voice from behind her says, “Rory?” And she nearly jumps out of her skin.

Rory whirls around to see Paris. “Paris? What’re you doing here? I wouldn’t have thought you’d go to this.”

“My parents made me,” Paris explains. “I have to stay until 8:30. Trust me, if I had the choice, I wouldn’t be caught dead here. I assume _you’re_ here with the boyfriend.”

“Oh, uh, no, actually,” Rory tells her. “I’m here with Jess.”

“Mariano?”

“Yeah.”

“He actually agreed to go?”

“I convinced him.”

“Interesting.”

Rory frowns. “What’s that supposed to mean?”

Before Paris has a chance to answer, Jess returns teddy bear free. “How many prizes are you planning on winning, ‘cause there’s only so much room in the car before I make you sit in the trunk - Geller,” he cuts himself off in surprise when he notices Paris.

“Jeez, do you two ever go anywhere without each other?” Paris scoffs. “You’re nearly joined at the hip.”

“Well, we just started using the bathroom all by ourselves,” Jess quips with a mischievous look on his face. “It’s a big accomplishment, if you ask me.”

Paris rolls her eyes. “I see that you couldn’t find a third stooge to join your little act for the night.”

“Jess is worth two,” Rory says. “Now, I want to play more games and get some food, so let’s wrap this up.”

Jess tries to elbow her, but she dodges. “Okay, okay. Guess we’ll see you around, Geller.”

“Wait - Paris, you can come along with us if you want,” Rory offers. 

Paris hesitates, looking between the two of them. “Are you sure?”

“Of course. It’s okay with you, right, Jess?”

Jess’ jaw is set, but he nods. “Nope. No problem.”

“Great.” Rory grins. “So, what do you say?”

Paris sighs. “I guess that doesn’t sound like the _worst_ thing in the world.”

“Definitely not,” Rory agrees. “Now I see ring toss, and I’m _really_ good at that, so let’s go!”

**

Two rounds of ring toss and one game of mini-golf later, Rory’s proved her worth at these games. Jess makes another trip to the car to deposit their prizes before returning with a new book. He keeps trying to sit down and read, but Rory continues to drag him along, ignoring his objections. “You have the rest of your life to read,” she scolds. “We only have three hours until we have to leave.”

Jess groans, but he complies in the end.

“I’m getting a little hungry,” Rory admits after a rather pathetic attempt at darts. “Paris? Jess?”

“I could eat,” Paris says with a shrug.

“There’s some food right over there,” Jess points out, pointing towards a food booth with some benches around it. “What do you guys want to eat?” He asks, taking out his wallet.

“You don’t ha-” Rory starts, but Jess cuts her off.

“Finish that sentence and you’ll regret it.”

“Chivalry isn’t dead after all,” Paris mutters to herself.

“Orders, going once, going twice…”

“A caramel apple. Ooh, and some popcorn. Please,” Rory adds.

“You’re going to get sick.”

“There’s no tilt-a-whirl, I think I’ll be okay.”

“Just a pretzel is fine,” Paris says to Jess, who nods in acknowledgement.

“Okay. I’ll be right back.” 

Once he’s gone, Paris turns to Rory with a suggestive look on her face. “So?”

“So...what?”

“So, what’s the deal between you two?”

Rory groans. “Not this again, please.”

“It’s a simple question!”

“And you have a take on it, I bet,” Rory guesses wearily.

Paris nods. “I do. I think he likes you.”

“Paris!” Rory exclaims, turning pink. 

“Hey, I’m just saying. He’s running back and forth to put your prizes in _his_ car, he’s buying you food-”

“He’s also buying food for you,” Rory points out.

“Whatever. My point is that-”

“Your point is what?” Jess asks, suddenly back with all the food. “And sorry, Rory, they were all out of popcorn. You’ll have to get sick another day.”

“It’s okay. This apple looks good enough to rid me of disappointment.” Rory takes the caramel apple from him gratefully. “And, uh, my point….well, my point was that-”

“Rory was just talking about how bogus the election was,” Paris cuts in. “And I agree. I mean, Gore winning the popular vote but losing the electoral college? Ridiculous. The Florida recount was major bull, too.”

Jess looks over at Rory skeptically, but she nods. “That’s it.”

“Checks out - it _was_ bullshit. So, what’s next?”

Rory grins. “Look at you, getting in the spirit of things.”

“Oh, no, don’t get me wrong. I just want this to be over as soon as possible, and doing things makes the time go by faster. Although, if you’d let me _read…”_

“You brought Wolfe. Might as well read _The National Enquirer,”_ Paris says distastefully. 

“Hey, _The Electric Kool-Aid Acid Test_ was-”

“Druggie propaganda. Can we move on?”

Rory’s eyes widen in exasperation. “Both of you, can it. Paris, if you don’t like it, just give him an Austen and he’ll be occupied.”

“As he should,” Paris sniffs. “Austen is only for people with actual _taste,_ though.”

“And what are you implying?” Jess asks.

“I want to go on the carousel!” Rory announces just to get Paris and Jess to shut up. “I still can’t believe they actually got one. Might as well test it out.”

“Count me out,” Paris says. “I get motion sick.”

“Any chance I can use that excuse?” Jess asks Rory. 

“Nope!”

“Hey, it’s not an excuse,” Paris objects, “it’s a medical condition. Look it up.”

“Do you mind if we go?” Rory asks with a slight wince. “If you do, we won’t.”

 _Say no,_ Jess mouths to Paris.

Paris just smiles knowingly. “Don’t mind at all,” she says, much to Jess’ disappointment. “Have fun, you two.”

**

Turns out, the best place to have a conversation isn’t a carousel. Rory _tries_ to talk to Jess, but while he insists on a stationary horse, hers moving up and down makes it quite difficult to talk without both of them dissolving into laughter. 

Soon enough, it’s time for Paris to go. Jess says goodbye and then excuses himself to go to the bathroom, leaving Paris and Rory alone.

“Thanks for, you know, letting me hang out with you guys,” Paris says sheepishly, not quite meeting Rory’s eyes. “It wasn’t that bad - although, Mariano’s taste in literature gets more questionable every time I talk to him.”

Rory laughs. “I’m sure he’ll say the same about you.”

“Probably - he’s stubborn like that. We’ll see each other Monday, I guess.”

Rory nods. “That’s the plan.”

Paris smiles. “Night, Rory.”

“Night.”

Once Paris is gone, Rory waits a couple minutes until Jess comes back with his hands behind his back and a mischievous grin on his face.

“What?” She nearly groans. “Nothing good can come out of whatever you’re hiding, I know that for a fact.”

“They have an ice rink, you know,” he informs her casually, taking a step closer.

“Yeah, I saw. What does that-” She stops herself. “You did _not.”_

“Oh, but I did.” Jess lifts up the two pairs of ice skates he’s holding. “I had to guess on your shoe size. Seven and a half?”

“That’s right,” she admits reluctantly. “Jess, what could have possibly led you to do this?”

He shrugs. “Thought it might be fun.”

“Jess, I am a horrible skater. Tonya Harding would be horrified.”

“Well, she’s banned from the United States Figure Skating Association for life, so I think you getting up using the wall is the least of her worries.”

“Well, how else are you supposed to do it?” When he quirks up a brow, she sighs. _“Fine._ But if I fall and bring you down with me, I don’t want to hear any complaints.”

“Sounds like a deal.”

“I hate you,” Rory grumbles, following him to the ice rink.

“Nah, you don’t,” he says with a smile. “I’m a minor inconvenience at the least.”

“Oh, yeah? Keep this up and see where it lands you,” she threatens.

“Are teddy bears flammable?”

“You wouldn’t dare!”

“No, I wouldn’t. See, minor inconvenience.”

She groans. “Let’s just get this over with.”

**

“Hey, you’re not doing half bad,” Jess says, gliding alongside Rory as she grabs onto the wall every two seconds for support.

She glares at him. “Shut up.”

“That was a _compliment,_ Gilmore. The polite thing to do is say ‘thank you.’”

“I’m not thanking you for anything while we’re still on the ice,” Rory grumbles, then yelping when she almost falls down.

Jess laughs and shakes his head. “Come on. I’ll help you.”  
She eyes the distance between his extended arm and the wall. “That’s too far.”

“It’s two feet at best.”

She gives him a wary look, but his gaze is steady, trustworthy, almost, so she hesitantly lets go of the wall. “Now push forward with your right leg,” Jess instructs her. She does so, nearly toppling over, but she grabs his arm just in time. He nearly falls down, but he regains his balance before it can happen.

“God, Gilmore, that was _so_ not smooth.”

“Don’t say I didn’t warn you,” she reminds him. 

“You’re right, you did.” Jess smiles at her. “Now let go of my arm and just hold my hand.”

“Nope. I’m good like this.”

Jess shakes his head amusedly. “Copy what I’m doing,” he says, gesturing towards his feet. Rory begins to follow his movements, pushing forward and gliding. “There you go, you’re getting it.”

“How did you learn to skate?” She asks, slowly letting go of his arm and gripping onto his hand instead. “You’re, like... _good.”_

He shrugs. “Taught myself. Went to enough birthday parties with ice skating and I caught on.”

“Oh.” She keeps her eyes fixed on her feet, making sure her movements are still matching his. “Never took any lessons, then?”

Jess snorts. “Wouldn’t have been able to afford it even if I had wanted to.”

“That’s true, lessons are pretty expensive.” 

“You didn’t take any either, I assume, based on your immense lack of skill.”

She gives him a look. “I didn’t, no. My mom’s not too bad, though. She’ll take me sometimes but all I do is fall down.”

“Well, you’ve never had such a talented instructor before,” he says with a smirk and a gleam in his eye. 

She smiles. “No, I guess I haven’t.”

“How about you move to my other side?” Jess offers, holding up their intertwined hands. “I can get circulation in this hand again and you can practice away from the wall.”

“Are you trying to make me look like an idiot?”

“No, that’s just an added bonus.”

_“Jess.”_

“Come on. Skate around me and then you can hold onto my arm ‘til your heart’s content.”

She glares at him, but she shakily lets go of his hand and lets him get a bit ahead of her before pushing forward. She gets one good slide in, but then the skate snags on a dent in the ice and she starts to fall forward. Fortunately, Jess’ arm is there for her to catch; unfortunately, she catches him off guard, and they both fall down. 

Rory starts to laugh, and Jess smiles. “Alright, that’s your last fall,” he says, somehow managing to stand up on his own. He offers her his hand and she takes it, letting him pull her up.

It’s when she’s straightened up and they lock eyes that Rory’s stomach bottoms out and her breath catches in her throat. It’s the first time she’s really looked at him since they started skating - she’d been too focused on watching her feet and being afraid to fall - and there’s just this intensity in his eyes, a tender look in them, and with his gaze fixed on her, everything from the last few months suddenly falls into place. 

_Oh._

She feels warm, warm down to her toes, even though it’s _so_ cold, it’s definitely below freezing. And in this moment, she realizes it’s because of _him._ God, this whole time, everything she’s been feeling, because of him, _for_ him - it all comes down to the same thing.

She likes him.

And Rory knows, she’s aware that she’s been denying it ever since she met him, but everyone else had to have been right because she does, she does, she has feelings for him. She’s done what all the books and songs and movies warned her about - she’s fallen for her best friend. 

“Are you okay?” He asks. He still hasn’t looked away.

She swallows and nods, trying to find her voice. “Yeah,” she says. It comes out a little hoarse. “Yeah, I’m okay.”

He smiles. “Good.”

As they continue to skate, Rory knows that whatever this is between them, everything has changed.

**

Jess gets her home ten minutes before eleven. She thanks him again and says goodnight, and then he drives off and it’s just her and the teddy bear she won at the start of the carnival. 

Rory opens the door and walks inside. “I’m home.”

“Kitchen,” Lorelai calls out.

Rory steps into the kitchen. Lorelai sits in a chair at the table, reading the newspaper. “Mom?” She says hesitantly.

“Yeah?”

“Can we call a truce?” Rory asks, her voice betraying her by wavering.

“Of course.” Lorelai looks up and when she sees the look on Rory’s face, she frowns in concern. “Rory, honey, what’s going on?”

“It’s about Jess.”

“What about him?”

Rory takes a deep breath, exhaling slowly and shakily. “You were right.”


	14. The Things They Carried

**Summary for the Chapter:**

> Rory learns a little about Jess' family. Luke admits a secret.

**Notes for the Chapter:**

> NOTE: I would like to clarify that my mention of the H*ntzbergers in the last chapter was NOT, in fact a nod to Logan. I hate that man, do not get me wrong. This has been a PSA, thank you.  
> Anyway...this one should be fun.

“You were right.”

Lorelai’s brow furrows in confusion. “Right about what?”

Rory looks at her mom, a little desperate, hoping Lorelai will pick up on what she means before she has to say the words out loud and make it real. _“Mom.”_

Lorelai stares at Rory for a second before- “Oh. Oh!”

Rory nods. Her throat is starting to hurt from holding off her tears. “Yeah.”

“Rory…” Lorelai trails off, unsure of what to say. 

“I know, I know,” Rory chokes out. “I _shouldn’t,_ but I just do. And I - I don’t think I can stop.”

“Honey, it’s okay.”

“It’s not. It’s not okay, mom, I - he’s my _best friend._ This just...this could ruin everything.”

“It’s going to be okay.”

Rory shakes her head. “It can’t be. I just - I don’t - and he - I can’t-”

Lorelai is up out of her chair with her arms around Rory the second she starts to crumble. Rory cries into her mother’s shoulder, gripping her tightly. “I’m gonna lose him.”

Lorelai smooths down her daughter’s hair comfortingly. “You’re not going to lose him.”

“How could I be so _stupid?”_ Rory croaks, pulling back from her mother and wiping her eyes furiously. “I mean, he’s my first real friend at Chilton, and he’s so good, mom, he is - he’s so smart and he’s got _so_ much potential, and he was there for me when I had no one else there…” She sniffs. “And then I just go ahead and throw it all away.”

“Rory, nothing’s happened,” Lorelai reminds her. “I know everything seems uncertain right now, but for all you know, he could feel the same way.”

Rory shakes her head. “No. No, and it doesn’t even matter if he does, because I-” She lets out a sob and covers her mouth.

“Rory?” 

“Dean,” Rory says, barely audible. “Dean. I am a _horrible_ person. I - liking two guys at once? Who _does_ that? I can’t - god, this is so unfair to him.”

Lorelai sighs. “You can’t help it, honey. People can sneak up on you like that sometimes.”

“It’s different with Jess,” Rory admits quietly. “I don’t know how, or why, but it just...is.”

“Well, you two are friends,” Lorelai suggests. “You didn’t start off as friends with Dean.”

Rory wipes her eyes again. “I don’t want to like him, mom, believe me. It’s so much easier being friends, and I just - now _everything_ is going to be different, and it’s my fault.”

Her mom rubs her arm comfortingly. “Take it a day at a time. You won’t know how different it’s gonna be until you see him again.”

Rory breathes in shakily, trying to steady herself. “You’re right. You’re right, I know, I just…”

“I get it. Let’s sit down, okay? Watch a movie or something, try to make you feel better.”

“I don’t deserve that.”

“We’re going to do it anyway,” Lorelai says firmly. 

Rory nods in agreement, and Lorelai steers her towards the family room. Rory slowly sits down on the couch, kicking off her shoes and taking off her coat.

Lorelai comes back with a tub of ice cream, which makes Rory laugh through her tears.

“This isn’t a breakup or anything, you know.”

“I know. But you’re still allowed to wallow.”

“I shouldn’t be,” Rory mumbles. “Don’t reward me for having feelings for two guys at the same time. Oh, my god, I’m a whore!”

Lorelai bites back a laugh. “You’re not a - Rory, stop with the ‘I’m so horrible’ bit for a minute, okay? Trust me, you’ll feel much better.”

“Fine.”

Rory falls over and rests her head on her mom’s leg. Lorelai strokes her hair with a smile. “Hey.”

“Hm?” 

“Why don’t you tell me about Jess?”

**

Jess is waiting for her as usual when Rory gets to school on Monday. He’s reading, of course - this time it’s _Fear and Loathing on the Campaign Trail ‘72,_ which instantly reminds her of Dean, and she just wants to turn around and run away. 

Instead, she puts on a brave face and walks towards him, trying (and failing) to ignore the way her heart picks up and the sudden sensations of a whole butterfly habitat in her stomach. 

“Hey, Gilmore,” he greets her with a grin. “How’s my favorite figure skater?”

“She’s good,” she says, a little bit louder than intended. “I mean - well, I don’t - my weekend was fine.”

Jess raises an eyebrow at her amusedly. “You okay? You seem a bit tongue-tied today.”

“Yeah. I’m just...tired.”

“Okay,” Jess says, but he still eyes her skeptically. “You ready for Medina’s class today? I heard he’s introducing a new project.”

“Another project?” Rory scrunches up her face in disgust. 

“I thought you liked projects.”

“Not when there’s an abundance of them.”

“Fair enough.” Jess plays with the strap of his messenger bag a bit as he looks down at her. The look in his eyes is enough to make her want to wonder - but she doesn’t. She can’t. “Is it safe to assume that we’ll be working together?”

“Yep,” Rory replies a little too quickly, feeling a blush creep up her cheeks. “Yep, it’s safe to assume.”

“Good. Working with Tristan on the last one was…” Jess shudders. “An _experience,_ to say the least.”

Rory makes a face. “I can’t _imagine_ having to work on a project with him.”

“Try to keep it that way,” Jess advises her. 

“Will do.”

He smiles again, and Rory averts her gaze quickly, her heart skipping a beat. 

He gives her a confused look. “Are you sure everything’s cool? You seem a bit off today.”

She nods. “Yeah, I’m - I’m tired, you know, with all the homework - they assign a _lot_ of homework here, really, and I don’t mind, but it’s still...a lot.”

Jess folds his lips to try to keep himself from laughing. “It is a lot. Good thing I don’t do it, or I’d be way more stressed.”

“You should be doing your homework.”

“What was that? Was that the bell? I better get going. I’ll see you!”

She gives him a look. “We have the same first period, Jess.”

“Couldn’t hear you!”

“The bell isn’t even ringing!”

“What was that?”

She rolls her eyes and jogs to catch up with him.

**

“I assume most of you went to the carnival,” Mr. Medina says, sitting on his desk, “and I truly hope that you all had a good time. However, that good time may or may not be ending, because - as I’m sure you’ve somehow heard - we will be beginning a new project today.”

The class groans.

He smiles good-naturedly. “Yes, yes, I know. I’m horrible. However, I think you all might enjoy this one somewhat.”  
“Good luck with that,” Rory hears Jess mutter. She leans forward and buries her smile behind her arms.

“Since we’re only two weeks from our ski lodge trip and then winter break,” Mr. Medina continues, looking amusedly in Jess’ direction, “I figured I’d go easy on all of you. So, your project is to watch a movie. But not just any movie - don’t go watching _American Pie_ or _The Spy Who Shagged Me_ and turn in your paper, okay?”

He holds up a book he has on his desk - _Hamlet._ “Pick a movie adaption of one of the books we’ve read this semester. Watch it - and actually watch it, please, you can’t find Cliff’s Notes for this - and then write a paper on the differences and similarities between the book and the movie. What did the adaption do well? What did it misinterpret? And yes, Mr. Dugray, you _can_ work with partners, but I’d advise you to pick one who you can actually get work done with.”

Rory covers her mouth to hold back a laugh. 

“And that’s the assignment; quick, easy, simple. Any questions before I move on?”

One girl raises her hand and asks him to list the books they’ve read. As he answers, Rory glances back at Jess and tries not to blush when she notices that he was already looking at her. 

_Romeo and Juliet?_ He mouths.

She grins and nods. _Definitely._

“Alright. Now, I have another announcement. I’m sure we’re all aware of the ski lodge trip - more information will be given at a later date - but there’s another exciting trip that the board has just organized. 

“After Winter Break, a handful of students will be able to go to New York. This trip is centered around journalism, with a spec of tourism.” Rory sits up alert when she hears this. “Students will be able to visit the _Times_ office, CBS, and a couple other locations that are to be determined. You can talk to me if you’re interested, and as long as the spots don’t fill up, registration will be open indefinitely.” The bell rings. “Have a good day and I will see you all tomorrow.”

As everyone packs up, Rory sees Paris make a beeline for Mr. Medina and she smiles.

Jess stops next to her on his way out. “You signing up?”

She shrugs half-heartedly. “Maybe.”

“You should.”

“Why? Trying to get rid of me?”

“Nah. I mean, getting to see the _Times?”_ He nudges her. “One step closer to the dream, right?”

“I guess.” She zips up her backpack and slings it over her shoulder. “So, we should talk about the project.”

He nods, brow furrowed in mock-seriousness. “Yes, we should.”

“Are you free to work tonight?”

“I never have any plans. You should know this by now.”

“Right.” She snorts. “Well, we can work at my place. You already know how to get there and you know my mom, so it works out.”

Jess hesitates. “How about where I live instead?” He offers. “We can take advantage of the home theater while I’m still around to use it.”

She frowns. “What’s that supposed to mean?”  
He ignores her question. “So, what do you say?”

Rory pauses to think it over. While she’d love to have Jess at her place, her curiosity might win this round. 

After a moment, she nods. “Sure.”

“Alright. We can meet in the courtyard after school, then.”

“Sounds like a plan.”

Jess makes his way towards the door; she follows him, but Mr. Medina calls after her, “Miss Gilmore, one moment, please?”

Jess looks at her questioningly and she signals that it’s okay for him to go. Once he’s out of her sight, Rory turns back to face Mr. Medina. “Hi, Mr. Medina.”

“I, uh, I just wanted to talk to you about the New York trip,” he says, a little awkwardly. “You’re striving to be the next...Christiane Amanpour, correct?”

“Something like that.”

“I think this could be a good opportunity for you, Rory. Please, consider it - I know we’d love to have you on the trip.”

“I will,” Rory assures him. “It does seem really interesting. I’m just a little unsure about going to New York so soon after the ski lodge trip. I don’t want to leave my mom alone for too long. You know her, she’ll go crazy,” Rory rambles, and then mentally slaps herself when she realizes her mistake. 

To her relief, he only smiles - albeit a little sadly. “Yes, I do. But you might not get another chance like this, so I really hope you decide to go.”

“I’ll keep that in mind. Thank you, Mr. Medina. It does - it means a lot to me that you think that.”

“Of course.”

“I should probably…” Rory trails off, glancing at the doorway behind her.

Mr. Medina nods. “Oh, yes, you do have more classes, don’t you?” He smiles. “Have a good day, Rory.”

“You, too,” she says kindly. 

Once she’s out of the classroom, Rory lets out a shaky breath, feeling her nerves settle just a bit. It feels like letting out a breath she hadn’t been aware of in the first place, knowing that things don’t have to be weird with Max - _Mr. Medina, really, Rory, you know better -_ after everything that went down between him and her mother. 

He might have a point, too - the trip does seem like a really good opportunity, one she definitely would not have had at Stars Hollow High. She guesses she’ll just see what happens, something she’s never been especially good at, but things have been changing, lately, anyway. 

But she’s considering it. She’s _definitely_ considering it. All she really needs is a push in that direction. 

**

(During lunch, Rory notices Jess’ eyes, his cheekbones, his hands, his _arms,_ and _god_ does she have it bad.) 

**

The drive over to Jess’ is unusually quiet. Typically, when she’s with Jess, silence is never uncomfortable, but even then it doesn’t last very long because at least one of them inevitably has something to say. Today, though, she feels incredibly awkward around him and can barely get two consecutive sentences out. 

(They stop at a video store to rent the movie. She doesn’t say a word the entire time.)

Jess drives up to an iron gate, then signals for her to wait as he climbs out and puts in the code. Once it starts to open, he gets back in and drives up the driveway to, frankly, one of the biggest houses Rory has ever seen.

“Here we are,” Jess grumbles, pulling to a stop in front of the house. Rory half expects a valet service to come out and take his car as she steps out. “Home sweet home.”

The doorway itself is impressive, fancy carvings in the wood, and Rory suddenly feels like she’s in another world. There’s art - a _lot_ of art - and she can’t help but notice the complete absence of any photos. It doesn’t feel so much a home as it does a museum. 

“Wow.”

Jess glances over at her with a grimace. “Yep.”

He looks incredibly out of place, surrounded by wood paneled walls and paintings and glass sculptures and a million other things that cost so much more than anything Rory owns. 

(As long as she’s known him - which, admittedly, hasn’t been very long, but still - he’s never really been comfortable in this world. She can’t blame him for it, of course. She feels the same way.)

“Everything here makes me feel small,” she blurts out. 

“I get what you mean,” he admits after a moment of hesitation. 

Jess starts up the stairs, but a door opens in the hallway and a man steps out. He’s definitely tall, taller than Dean (maybe not by much, but still), maybe in his forties or fifties. He’s got graying hair and a collar buttoned so high she can’t imagine he can breathe. _This must be his stepfather,_ she thinks. 

“Oh, Jess, you’re home.” He glances towards Rory. “Who is your, uh...friend?” 

“This is Rory,” Jess says, gesturing towards Rory, who gives the man a little wave and then mentally curses herself for it. “We’re working on a project.”

The man’s eyes narrow. “I’ve heard that excuse before. Just leave the door open, okay?”

Rory turns a bright red, but Jess is immovable. “Didn’t peg you for a voyeur, but whatever.”

Jess’ stepfather sighs in exasperation. “I don’t know what to do with him sometimes,” he says, and Rory realizes he’s talking to her. “But I guess it’s not up to me, is it? It’s either up to him or CPS.”

Rory lets out a shaky laugh, unsure of what else to do. 

He waves a hand dismissively. “But no matter. At least he’ll have someone to visit him when he’s cleaning bathrooms at a gas station off of I-84, right?”

Rory’s eyes widen, caught off guard, surprised that this man would say something so offhandedly _cruel_ about his own stepson. She knows Jess told her about him, she does, but it’s something else entirely to hear it for herself. 

(She glances back at Jess. There’s a tick in his jaw that wasn’t there before, and she looks away quickly, feeling like she might cry.)

“It was very nice to meet you, Rory,” he says congenially, but it feels _very_ fake. “I’m-” His cell phone rings, and he holds up a finger, answering the phone. “Roberts, I _told_ you, it’s a no on Gurman-Driscoll. What do you mean, I didn’t say anything about that?” He disappears into his office and the door clicks shut behind him. 

“So, that was your stepfather?” She asks, not knowing what else she could possibly say.

Jess nods curtly. His hand is gripping the bannister so tightly that his knuckles are white. 

She reaches over and puts her hand over his, letting out a breath when she feels his hand relax. “Well, I have to tell you, I’ve never met anyone nicer.”

She sneaks a peak at Jess, and feels pleased when she sees a hint of a smile on his face. 

“No, really, he makes my grandmother look like Mr. Rogers.” He shakes his head in amusement. “Wait, that didn’t make sense, did it.”

“Nope. But I understood what you meant.” He puts his other hand on top of hers for a brief moment before pulling back completely. “Let’s just...keep moving.”

She follows him the rest of the way up the stairs, and she has so many things she wants to ask him, but she knows it’s not the right time, so she files them away for another time. _(Where’s your mom? Where’s your step-brother?_ Etc, etc, etc.)

“Here’s the home theater,” Jess tells her, opening a door in the hallway. “Do you want some popcorn?”

“Sure,” she says, sinking into one of the seats. 

He sets up the video and sits down next to her with some popcorn. She immediately grabs some and stuffs it in her mouth, and he gives her a look.

“I was literally about to hand it to you.”

“Couldn’t wait,” she says, mouth full of popcorn. 

He rolls his eyes. She swallows and studies his face for a moment, wanting to reach out and stroke his cheek. He looks so tense, and it’s killing her. 

“Jess...are you okay?”

He lets out a heavy sigh. “I’m fine.”

She knows that’s not the case, he’s obviously not fine at _all,_ but she bites her lip and settles back into her seat.

(His hand finds hers only a few minutes in. _This is fine,_ she tells herself, trying to ignore the way it makes her heart skip a beat. _We’re just friends. That’s all this is. Don’t go thinking it’s anything more.)_

(Throughout the movie, she glances over at Jess repeatedly and blushes when he catches her looking.)

**

(When Jess drives her home, she tries to check the mailbox for a name, but it’s covered in snow.)

**

“Here’s your artery cloggers.”

Rory snorts, taking the plate from Luke gratefully. “Thanks, Luke.”

“Seriously, I don’t understand how you and your mother eat those things constantly.”

Rory taps on her notes with her pencil. “Brain food.”

“Right, right.” Luke gives her a look. “You okay, though? You’ve seemed a little down tonight, and I was just...wondering.”

“I’ve just got a lot of verb conjugations to memorize.”

“Rory, you love studying. I’m not buying this. You don’t look so good, and I _know_ it’s not because of your french homework.”

“Well, I have these french fries to keep me company. Maybe it’ll help me feel better _and_ learn my verbs.”

“French fries were invented in Belgium.”

“God! You’re right, I knew that,” Rory exclaims. “How could I forget?”

Luke raises an eyebrow. “Just admit you’re not doing too good and we can move on from there.”

Rory sighs. “Fine. It’s just...I went to my classmate’s house in Hartford to work on a project, and...god, his family is _horrible,_ Luke. His mom and step brother weren’t even there, but his stepfather was so rude to him...it was awful.”

“Sounds awful,” Luke agrees. “Guess we’ve all got family issues, don’t we?”

“I guess.” Rory takes a fry and pops it into her mouth. “Doesn’t make it okay, though.”

“You’re right.”

“I care about him a lot,” Rory admits quietly. “And I hate seeing him belittled by his own family like that, or by anyone. You should’ve seen his face. He said he was fine, but I know he wasn’t. But he wouldn’t even talk to me about it.”

Luke sighs. “My nephew is in a similar situation. But you know, sometimes we can only do so much. If your friend doesn’t want help, then you just can’t help him.”

“I _hate_ that.”

Luke smiles sadly. “I know. You get that from your mom, you know - that urge to help other people figure things out.”

“Sometimes I wish I didn’t.”

“Well, my…” Luke grimaces. “Nevermind.”

“You can tell me, Luke,” Rory says sweetly. “I like talking to you.”

Luke waves his hand in dismissal. “Nah, you don’t want to hear this. Too depressing.”

“I promise you I do.”

Luke hesitates. “Have I, uh, have I told you about my sister before?”

Rory sits up straighter, eyes wide. “No - my mom told me what you told her, but…”

Luke nods grimly. “Yeah, well...there’s kind of one big thing that I _didn’t_ tell your mom.”

“What?” Rory asks, starting to feel a pit of dread in her stomach. 

Luke hesitates for a moment. “She’s dead,” he says finally.

Rory’s eyes widen. “Oh, my god, Luke, I’m so sorry, I had no idea.”

Luke shakes his head. “I wouldn’t expect you to.”

“How long…?”

“Not long. About seven months.”

“Wow. I...I had no idea,” she repeats, unsure of what to say. “How did she…”

“Alcohol poisoning,” Luke tells her somberly. “I mean, I guess we all got used to the drinking, but after she remarried, it got...bad. Her son - my nephew - he’s the one that found her. Called nine-one-one, but...it was too late.”

“God, Luke, I’m so sorry.” 

He half-shrugs. “There was nothing I could do,” he says, but Rory can tell he’s thinking something very different. 

“Still.”

He gives her a sad smile. “Do you want a danish? It’s on the house.”

“Oh, yes, please.”

He nods. “Good luck with your studying.”

“Thanks, Luke.”

One danish later, Rory’s head is still spinning. She never would have guessed that that was the case with Luke’s sister, but it makes her think. Could something just as horrible have happened to Jess’ mom?

She can’t help but feel like there’s one, big crucial part that she’s missing. 

**Notes for the Chapter:**

> So...yeah. Wonder if anyone saw that one coming...


	15. Sense and Sensibility

**Summary for the Chapter:**

> Mr. Medina announces the sophomore ski lodge trip.

**Notes for the Chapter:**

> Sorry this is a little later than usual, but here we are!

“One week until the sophomore class leaves for the ski lodge,” Mr. Medina announces near the end of class. “Now, I know we’ve discussed this lightly, but as the head chaperone, I have been asked - nay,  _ required _ to lay down the rules and field any questions you all might have.”   
Rory pauses putting her books in her bag and leans back in her chair, only half-heartedly listening. Ever since the trip was informally announced, she’d had zero interest in going, so there’s no point in paying much attention. 

Mr. Medina leans back against his desk, surveying the class. “We will leave next Friday. You all need to be here bright and early - no later than six in the morning.” The class grumbles. “We will leave that Sunday and be back around three in the afternoon. We will be taking a bus both ways, so make sure you’ve got your motion sickness medication ready.” 

Paris mutters something under her breath that Rory doesn’t quite catch.

“It will be two to a room,” Mr. Medina continues, “and assignments-”

“Are roommates assigned by gender?” Tristan calls out.

She hears Jess snicker behind her and she folds her lips to prevent herself from laughing as well. A second later, she feels a tap on her shoulder and he slips a note onto her desk.  _ Wonder who the unlucky girl is that prompted him to ask that question. _

Mr. Medina sighs. “Yes, Mr. Dugray, they are. There will be no ski lodge babies made on this trip.” There’s a scatter of uncomfortable laughter before Mr. Medina clears his throat. “As I was saying, two to a room, assigned by gender. Room assignments will be assigned  _ at  _ the lodge, and no sooner.”

Tristan raises his hand, but doesn’t bother to wait to be called on. “Can we request room assignments? Or ask  _ not  _ to room with someone?”

_ And I wonder who the unlucky guy is that prompted him to ask  _ that  _ question,  _ Rory scribbles on the piece of paper before subtly handing it back to Jess. His fingers brush against hers and linger for a moment, causing her breath to hitch in her throat.

(Jess sitting directly behind her has served to be more of a  _ distraction  _ than anything these past couple weeks since the winter carnival.)

_ Very funny,  _ Jess writes back.

_ Well, knowing our luck… _

She hears him laugh.  _ Please, do not finish that sentence. _

She glances back at him, but when he catches her looking, she averts her gaze quickly and crumples up his note in her hand for lack of anything better to do.

“And that concludes our little Q&A session,” Mr. Medina concludes with a clap of his hands, and Rory realizes she’s zoned him out for god knows how long. “The bell should be ringing…” The bell rings. “Now. Mr. Mariano, please stay back for a moment - the rest of you, have a great rest of the day, and don’t forget to do your readings.”

Rory puts on her backpack and meets Jess’ gaze. “You want me to…?” She trails off, glancing towards the doorway.

Jess laughs. “Go wait in your usual spot. I know you want to hear.”

“Hey, I-”

He holds a hand up. “I’m giving you a pass, Gilmore,” he says, that usual crooked smile on his face. “Take it.”

Rory slips out of the room, hanging back just outside the doorway against the side of the lockers. She sees Jess pull up a chair and sit down like he’s got this routine down to a point. 

Mr. Medina takes a seat behind his desk. “How are you doing today, Jess?” 

Jess shrugs. “Fine, I guess.”

“Well, that is an improvement. Last time I asked, you didn’t even answer, so I assume it was pretty dismal.”

“Can we just get this over with?” Jess snaps, but then he seems to regret it and adds, “please.” 

Mr. Medina simply smiles. “Yes, yes. You’ve been doing a lot better in this class, lately, Mr. Mariano, a lot better. But all those months of - well,  _ not  _ doing well are still holding you back.”

Jess fidgets uncomfortably. “I thought you said that if I did well on the upcoming assignments-”

“Unfortunately, it wasn’t well enough.”

“But I-”

“Jess, I am offering you a chance to save your grade and  _ pass _ this semester,” Mr. Medina says evenly. “You can take it or leave it, but I think you should take it. However, it is entirely up to you.”

Jess hesitates. “What is it?” He asks, an ounce of hope in his voice. 

“The lit mag is accepting submissions after winter break,” Mr. Medina informs him. “Any form of writing - poetry, short stories - well, I guess just those two. But I will offer you extra credit to write a story to hand in to me after winter break.”

“Hey, wait a second, I-”

“You don’t have to publish it,” Mr. Medina continues. “I won’t dock points if you don’t. But write something, give it to me, and if you actually take the assignment seriously, I will give you extra credit and you will pass this class. And who knows, you might end up wanting to publish it after all.”

“I wouldn’t count on that,” Jess mutters, picking at a loose thread on the strap of his messenger bag.

Mr. Medina sighs. “So, what do you say?”

It takes Jess a few seconds before he responds. “Fine. I’ll write it.”

“I’m very glad you’ve decided to do it. I don’t think you’ll regret it.”

Jess grimaces. “Yeah, we’ll see.”

“Indeed we will.” Mr. Medina leans back in his chair. “You’re very talented Jess, more than you give yourself credit for. I think this will definitely be good for you.”

“I already agreed. You don’t need to keep trying to convince me.” Jess looks down at his lap. “But...thank you. For this. I guess.”

“Of course. Now, you should probably start heading out. I think Miss Gilmore is getting a little antsy out there.” Rory turns a bright red and ducks out of sight. She hears Mr. Medina chuckle and she flushes even darker. “I do have one more thing to talk to you about, but...in private. Would you mind closing the door for a moment?”

She hears Jess get up, and then he pokes his head out of the doorway and smiles. “I’ll be right out.”    
Rory nods, still embarrassed. He lingers for a moment before closing the door, and Rory lets herself exhale. 

“What the hell are you doing?”

Rory whips around in surprise to see Paris. “Oh, my god, you scared me,” she breathes, pressing a hand to her chest.

“God, you’re an easy scare,” Paris says, rolling her eyes. “And a little over dramatic. I never would’ve guessed.”   
“What do you want, Paris?”

“I wanted to...ask you something. About the ski lodge trip.”

“Oh.”

“Are you going?” 

“Uh...probably not,” Rory says awkwardly. “I don’t really have any close friends besides Jess, and I doubt he’ll want to go, so. Plus, Dean.”

“You’re not going.”

Rory shakes her head. “No.”

Paris groans. “Come  _ on,  _ Gilmore. I cannot be alone the entire time. I’ll go insane.”

“You’re going?” Rory asks in surprise. 

“My parents are making me go,” Paris explains flatly. “Personally, I’d rather spend the weekend in hell, but I guess that froze over, so…”

“You have Madeline and Louise.”

“Please. You  _ know _ they’re going to ditch me for guys the minute they get the chance,” Paris snaps. “Look, we may not be  _ friends,  _ but you’re the only other person here that doesn’t give me a headache just by talking to me. And I don’t need to be popping pills the entire weekend just so I don’t get a migraine.”

Rory grimaces. “I don’t know…”

“You don’t even have to ski,” Paris continues. “You can just read or make out with Mariano, I don’t care, but you  _ have _ to go.”

Rory flushes. “Hey, I have a boyfriend. I’m not going to  _ make out with Mariano.” _

“You two aren’t convincing anyone. Even if you’re not together, you will be eventually. A guy doesn’t stare at a girl for an entire class if he isn’t in love with her.”

“He’s not-” Rory huffs. “Why would you - why do you even think that? Maybe he just...likes my hair,” she finishes lamely.

Paris looks at her flatly. “Please, you are not that naive. I don’t know why you refuse to acknowledge it, but the guy’s into you. Big time.”

“You’re cracked!”

“Just go on the trip, okay? I could care less if you two decide to reenact the whole Cory and Topanga bit, but I can’t be alone the whole time.”

Rory grimaces. “...Fine. I’ll go.”

Paris smiles triumphantly. “Good. I’m glad.”

Rory opens her mouth to speak, but she hears voices approaching the door and soon enough, it swings open and Jess walks through. 

“I’ll see you in class tomorrow,” Mr. Medina says to him.

Jess nods. “Thank you.”

Mr. Medina smiles and closes the door.

Jess turns to Rory with a sigh. “Alright. I’ll walk you to - what’s Geller doing here?”

“Nothing,” Paris answers before Rory can even open her mouth. “Nothing at all. You two have a good walk to class,” she adds with a knowing look in her eye before turning and walking away. 

“What was that all about?” Jess asks, bewildered.

“She’s just being...Paris,” Rory replies with a shrug, trying not to flush under his intense gaze. 

“Fair enough. I’ll walk you over,” he says, nudging her in the side. She nods and walks alongside him, unable to stop thinking about what Paris said, and trying furiously not to blush every time Jess looks at her. 

**

Dean comes over that night for pizza and a movie. Rory keeps glancing over at him anxiously throughout the movie  _ (The Muppet Movie,  _ as per Lorelai’s request), bouncing her leg absentmindedly. Eventually, Dean sighs and turns to face her. “Okay, I’ll bite. What’s going on?”

“I’ll get some more popcorn,” Lorelai suddenly announces, not-so-subtly scampering out of the room.   
“You think she’s trying to give us privacy or something?” Rory asks with a laugh. 

Dean gives her an unimpressed look. “C’mon, Rory, I know you. What’s wrong?”

Rory stares down at her feet. “So my school has this class trip for the sophomores every year where we, uh, we go to a ski lodge in upstate New York.”

“Uh-huh.”

“And, I, uh - well, I kinda told my friend that I’d go. I was kind of bullied into it, but, you know.”

“This...friend. Was it Jess?”

Rory purses her lips together, trying to stay calm. “No, actually it was Paris.”

“Well, is Jess going?”

“I don’t know,” Rory returns. “Maybe. But that’s besides the point. I leave next Friday and I came back that Sunday, so it’s just a few days where we won’t see each other.”   
Dean blinks a couple times. “So you’re going on the class trip  _ next _ weekend?”   
“Yeah.”

“We had plans.”

“We can reschedule,” Rory offers anxiously, pulling her sweater over her hands absentmindedly. “Please don’t be mad. Paris really wants me to go, and I don’t want to just back out. And who knows, I might have a good time after all.”   
Dean hesitates for a moment. “I don’t want you to go,” he says finally, not looking at her.

“Dean, I-”

“I don’t want you to go,” he repeats, more firmly this time. 

“I - but...why?” 

He sighs heavily. “I like spending time with you, Rory. And you’re going on this - this trip at a  _ lodge,  _ with other  _ guys-” _

“Are you really still making this about Jess? I don’t even know if-”

“It’s not just Jess,” Dean interrupts. “It’s about Tristan, too.”

“So you don’t trust me not to cheat on you on a two night trip.”

“It’s not you I don’t trust. It’s them.”

Rory tries to push her anger down as she looks at him, incredulous. “What’re they gonna do? Pressure me into cheating on you because I’m so weak willed?”

“Hey, you got pressured into going on the trip. I’m just basing this off of facts.”

“By Paris! She’s a friend!”

“You’re always saying that Jess is just a friend,” Dean points out. 

“Jess would never pressure me into-” She cuts herself off, knowing what direction her words would take if she let herself keep talking. “Dean, I’m not asking for your permission.”

“Well, it  _ sounded  _ like you-”

“Okay!” Lorelai interrupts loudly, walking back in with a bowl full of popcorn. “I think I put a little too much butter in this, but the more the merrier, right?”

“Right,” Rory says, glancing at Dean anxiously.

“Dean, you want some popcorn?”

“No thanks,” he grumbles, still glaring in Rory’s direction.

She’s a little choked up for the rest of the movie.

**

After the movie, Dean says goodnight. Rory apologetically hands him his coat, but his hand doesn’t linger on hers like he usually means to and his expression remains dark.

“Goodnight, Dean,” she says, and leans up to kiss him. When she pulls back, he’s relaxed a little, but he still looks mad.

“Goodnight, Rory.”

“I’ll see you tomorrow?” She asks nervously.

“Yeah, I guess.”

“Good.”

He nods and shuts the door behind him.

Lorelai follows Rory into her bedroom, hands on her hips. “Okay, you want to explain what’s going on with Grumpy McGrumperson?” She demands, gesturing towards the front hall.

Rory plops down on her bed. “Nothing. I was just telling him about the ski lodge trip.” She doesn’t meet her mom’s eyes. 

Lorelai sits down next to her daughter, looking concerned. “It seemed a lot like an argument.”

“It almost became one,” Rory admits. “He really doesn’t want me to go.”

“Yeah, it sounded like it.”

“I don’t know what I did,” Rory chokes out, willing herself not to cry. “It’s like he doesn’t trust me, and I can’t think of anything I did to warrant that.” 

“Oh, honey…” Lorelai wraps her arm around her, bringing her closer. “You didn’t do anything.”

“Then why was he so mad?”

Lorelai sighs. “I don’t know. But...honey, if he-”

“No,” Rory cuts her off, sitting up and shaking her head. “No, please don’t make this into...I don’t even know. It’s just a fluke.”

“Rory…”

“Mom, please.”

Lorelai looks like she wants to argue, but she sighs and relents. “Okay. But...okay.”

“It’s gonna be fine,” Rory says unconvincingly. “I’m gonna have a good time, and he’ll be happy to see me when I get back.”

Lorelai bites back her words and nods. Rory does her best to ignore the look on her mom’s face.

“It’s gonna be fine,” she repeats, but she doesn’t quite believe it.

**

“So, you’re going on the ski lodge trip?”

Rory nods glumly. “Paris nearly twisted my arm out of my socket, but I agreed to go.”

Jess snorts. “Well, there’s a sucker born every minute, right?”

“Hey!”

He shakes his head amusedly. “Did you tell Dean that you’re going?” Jess suddenly asks, glancing over at her. 

Rory scowls and kicks at the wall she’s sitting on. “Yeah.”

“Woah, that is not the usual reaction you have when I mention the boyfriend. Is something going on?”

“Nothing’s  _ going on,”  _ Rory mumbles, “it’s just...he’s...he picked a fight when I told him I was going. Or, it would’ve been a fight, but my mom cut in before it could become one.”

“He didn’t want you to go?” Jess guesses. 

Rory shakes her head. “No, he did not.”   
“Why?”

Rory bites her lip. “He’s just - I don’t know.”

“I think you do,” Jess returns. 

“Oh, you?”

“I do,” he confirms. “I just think that you don’t want to tell me.”

She looks over at him, expecting to see anger on his face, but instead he looks concerned.

Rory sighs. “I really don’t want to talk about it, Jess. Please, can we just...drop it?”

He nods. “Yeah.”

“Thank you.”

They sit there in silence until Rory speaks up. “Are you going?” She asks, even though she thinks she knows the answer already.

He surprises her by shrugging. “Not sure. I mean, on one hand, it’s a trip, but on the other hand...it’s a trip.”

“You know what I think?”

The corner of his mouth quirks up. “What?”

She holds her chin up. “I think you should go.”

“Yeah?”

“Yeah, I do,” she replies firmly. “It’s only a few days. Plus, it’s a lot of time for us to hang out because I assume neither of us will be skiing.”

Jess looks unconvinced. “What about Paris? She’s the one who wanted you to go.”

“I mean, I’ll spend some time with her, but she’ll probably get sick of me eventually.”

“What does she expect you to do when you’re not with her?”

Rory blushes when she remembers what Paris said about  _ making out with Mariano.  _ “We won’t have to worry about that if you go.”

“I don’t know, Rory…”

“Please?” She says. “I mean, you like spending time with me, right?”

“Eh. You’re tolerable.”

She rolls her eyes. “Besides,” she continues pointedly, “it’s time away from your step-dad, right? And your mom?”

Jess’ expressions hardens and Rory’s eyes widen as he remains silent. She must’ve struck a nerve, and she scrambles to undo it. “I shouldn’t've said that, Jess, I’m sorry. I shouldn’t be bugging you about this, either, that’s not fair of me. I’m sorry, I - I’m just - I’m-”

“Rory,” he says, cutting her off with a slight laugh, “it’s okay.”

She looks at him with a slight grimace. “Yeah?”

“Yes,” he assures her, his gaze unwavering.

“You’re not angry?”

“Not at all.”

She sighs in relief. “Okay. Good.”

“It’s actually kinda nice,” he adds. “You know, that you want me to go and all.”

Rory smiles softly. “So?” She asks with a slight wince.

Jess exhales slowly, then looks back over at her. “I’ll go.”

She bites back a grin. “You’re going on the trip?”

“I might live to regret it, but...yeah. I’ll go.”

“You’re going on the trip?” She repeats, utterly dazed.

“It’s free, right?”

“You’re going on the trip.”

He cocks his head to the side. “You’re sounding a bit like a broken record there, Gilmore.”

“I just can’t believe that you agreed to go.”

Jess smiles. He straightens back up and Rory realizes just how close to her he had been leaning. “It can’t be too bad. I doubt much happens on these trips.”

“Not if Mr. Medina has anything to say about it,” Rory agrees. “What did he say? No ski lodge babies?”

Jess snorts. “Something like that.”

“Thank you,” she says seriously. “It - it means a lot to me that you’ll go.”

He shrugs, but he looks pleased. “No problem.”

“Was I right in assuming that you’re not gonna ski?”

“I’m offended. I’m a black diamond champion, I’ll have you know.”

“Okay, I can’t tell if you’re kidding or not.”

“You know me pretty well. I think you can figure it out.”

Rory grins. “Yeah. I do.”

The look in his eyes causes her heart to pick up. “Better than anyone.”


	16. Things Fall Apart

**Summary for the Chapter:**

> At the Chilton ski trip, Rory makes a decision that could cost her her friendship with Jess.

**Notes for the Chapter:**

> I'm so sorry it's been over a week since I last posted! I think I hit a bit of a writing slump, but hopefully that won't happen again and I can keep posting more consistently.   
> Hope you guys enjoy this one - it's a bit of a doozy.

“Okay, uh, toothbrush?”

“Check.”

“Tooth _ paste.” _

“Check.”

“Uh...hairbrush.”

“Yep.”

“Can I move on from toiletries now?” Lorelai asks, looking up from Rory’s (annotated) packing list. “Also, why is there a  _ lewd  _ joke written next to ‘feminine products?’”

“Oh, that was Jess,” Rory says, laughing a bit to herself as she leans over to look at the list. “He took my copy during lunch and wrote some stuff on it.”

Lorelai gives her daughter a wary look. “He’s going on this trip too, right? Jess?”

“Yeah.”

“And how are you feeling about that?”

“What do you mean?”

Lorelai sighs. “I mean, are you excited? Worried? I can’t quite work out the vibe here, Rory. I need you to spell it out for me.”

“Well, I invited him, I’d better be excited,” Rory replies, trying to keep smiling.

“You know what I mean,” Lorelai says gently. 

Rory stares down at her lap, unwilling to make eye contact. “It’ll be nice,” she says with more resolve. “No matter how I feel about him, it’s not like anything can change on a two night trip. Especially if he doesn’t feel the same way about me.”

“Does he?”

“No,” Rory replies immediately, but she’s trying to convince herself more than her mom. “He doesn’t. I mean, he  _ can’t _ , right? That would be...just…” She shakes her head. “No, he doesn’t. He can’t.”

Lorelai nods; however, Rory doesn’t think she’s quite buying it. “I’m sorry.”

“Mom, don’t be sorry,” Rory insists with a half-laugh. “It’s gonna be fine. So what if I like him, right? I’ve got a boyfriend I’m coming home to, anyway, so I should just focus on missing him instead of…” She trails off.

“Speaking of Dean…” Lorelai hesitates. “Did you ever smooth things over with him?”

Rory bites the inside of her cheek. “No,” she admits. “He didn’t call.”

“That’s a first.”

Rory nods. “Yeah.”

There’s a moment of silence before Lorelai claps her hands together. “Okay. Continuing with the checklist, right? Where were we...aha! Clothing and accessories…” She drags her finger down the list. “Pajamas?”

“Two sets, just in case.”

“That’s my girl.” Lorelai smiles. “Two pairs of pants - comfortable to walk in, too, they specify that right here.”

“Yep!”

“Three shirts?”

“I packed an extra.”

Lorelai goes through the rest of the clothing and accessories  _ (they’re all accounted for!) _ before beginning to fold up the list. “Seems like you’re prepared.”

“Wait, you forgot rain gear!”

Lorelai gives her a look. “Honey, it’s not supposed to rain.”

“Well, it doesn’t hurt to be prepared, right?”

“Oh, my mother would be proud…” Lorelai mutters, shaking her head. “Okay. Rain gear? Snow gear? ...Hail gear?”

Rory remains unimpressed. “I’m thoroughly prepared for any type of weather.”

“And how heavy is your bag?”

“A lot lighter since I moved all my books to my backpack.”

“And that’s more or less than the entire inventory of Stars Hollow Books and the library combined?”

“To be fair, there’s not a lot of books in the library,” Rory points out.

Lorelai eyes the yellow backpack at Rory’s feet. “And they’re all in there?”

“Okay, bye.” Rory begins to open the car door, but Lorelai grabs the back of her coat so she can’t leave the car. “Wait, you can’t leave without saying goodbye to your  _ mother!” _

Rory settles back into her seat and gives her mom a look. 

Lorelai’s mouth twitches as she tries not to smile. “I’ll stop teasing, I promise. Even if you’re going to cause the bus to move infinitely slower due to your bag of bricks, and you won’t even make it to the lodge, and you’ll have to resort to -  _ fine,  _ fine,” she says when Rory opens her mouth to object.

“We’ll be back at three on Sunday,” Rory reminds her sternly.  _ “Please  _ do not be late.”

“When have I ever been late to pick you up from these things?”

Rory gapes at her. “Do you not remember my field trip to Hartford in fourth grade? I had to wait  _ three hour _ s until you showed up.”

“Hey, you got to hang out in the teacher’s lounge, so I don’t remember much complaining,” Lorelai retorts. “And fourth grade? Really?”

“You’re not the only one who can hold a grudge,” Rory responds, the corner of her mouth quirking up.

“Ah, but I am the master.”

“Can’t argue with that.” 

Lorelai smiles. “So have fun, okay? I want to hear  _ all  _ about it when you get back. Including the dirty details,” she adds with a brow raised suggestively. 

Rory rolls her eyes. “Mom, it’s a school trip. No one’s gonna...you know.”

“Oh, my sweet, sweet, innocent daughter,” Lorelai coos, smoothing down Rory’s hair before Rory swats her hand away. “I bet at least one couple-”

“Okay! Time for me to go!” Rory exclaims. 

“I guess I should let you go,” Lorelai pouts. “This might be the longest amount of time that we’ve ever spent apart,” she adds woefully.

“We’ll just have to make up for it when I get back.”

“Movie marathon?” Lorelai asks hopefully.

Rory nods. “Totally. Ooh, we can order Al’s - isn’t he switching back to Chinese food on Saturday?”

“Al’s it is.” Lorelai smiles and then hugs her. “Have a great time, okay?” She says, pulling back.

“I will.”

“Good.” 

Lorelai lets Rory get out of the car this time, and Rory waves before turning and walking towards the courtyard where her classmates are waiting for the bus. 

(She hears the Jeep drive away and resists the urge to look back. It’s almost pathetic that she misses her mom already.)

She looks around, but she doesn’t see Jess yet, so Rory hops up on one of the half walls and takes a book out of her backpack. Admittedly, she  _ did  _ bring a lot, but in her defense, she figured she’d end up sharing with Jess and it’s always nice to have options. 

Thankfully, Luke opened the diner extra early for the two of them so they could get coffee and breakfast before heading to Chilton, so Rory takes a sip of her coffee and begins to read. She’s barely been reading for five minutes when she’s interrupted by Paris. 

“Rory,” Paris snaps. Rory, startled, nearly falls off the wall, but she regains her balance just in time.

“Hey, Paris,” she replies a little breathlessly, setting her book down beside her. “Good morning.”

“Maybe for you,” Paris mutters.

“Not a morning person, huh?” Rory guesses.

Paris ignores her. “I put in a request to have you as my roommate,” she informs Rory, forgoing any other greetings. “Now, we’re not  _ technically  _ allowed to do that - some lame attempt at fairness, but it’s just coddling because there’s plenty of exclusion in the real world - but I slipped a note on Medina’s desk a couple days ago asking him.”

“You didn’t threaten him, did you?” Rory asks wearily.

“Yes, Rory, I pulled a knife on him and demanded he assign us to the same room.” Paris rolls her eyes. “Get all your dumb questions out early, I won’t have the patience for any more.”

“Isn’t there no such thing as a dumb question?”

“That’s what they say to idiots to make them feel better,” Paris says flatly. “Look, you’re the only person who I wouldn’t want to smother in their sleep. Or who wouldn’t kill  _ me.” _

“Not Madeline and Louise, huh?” Rory asks, wishing her coffee was just a little bit stronger. 

“You think they’re not gonna be bringing back boys? I’d rather be dead than have to hide out in the bathroom while one of them gets lucky.”

_ Guess I’ll have a story for mom after all.  _ “Fair enough,” Rory sighs. “But why me? I mean, I was surprised when you asked me to go on the trip, and this…” She shakes her head. “You hated me, like, a month ago.”

“I can tolerate you now.” Paris eyes Rory’s book and groans when she sees the title.  _ “Fear and Loathing in Las Vegas?  _ Really? I can’t  _ believe _ you’re reading Hunter Thompson.”

“My boyfriend said I should read it,” Rory says a little defensively. “It’s not bad.”

Paris’ nose crinkles. “Your boyfriend probably looked up ‘books to tell my girlfriend to read’ online because if  _ this  _ is his selection…” She shakes her head.

“I told him to read Austen.”

“Well, you have some taste.  _ He  _ does not.”

“Fine, I’ll switch it out for now, okay?” Rory takes out _The Tell-Tale Heart and Other Writings_ from her bag, but Paris shakes her head.

“How can you stomach Poe at six in the morning?” 

Rory rolls her eyes and takes out  _ On the Road.  _ Paris scoffs. 

“Now you’re just trying to spite me.”

“You hate the Beats, too?”

“Neal Cassady can kiss my ass,” Paris says in response.

“Well, that’s not very friendly.”

Rory looks up and immediately brightens when she sees Jess. “Hey,” she breathes, trying to hold back a grin.  _ (Get it together, Gilmore.) _

“Hey, Gilmore,” he replies warmly. “You got enough coffee to keep you upright?”

“Probably not. I’ll probably crash on the bus, so get ready to catch me.”

Jess laughs before turning his attention back to Paris. “So, what was that you were saying about Cassady?”

“We’ve been over this, Mariano,” Paris snaps. “The Beats were self indulgent and didn’t know how to end a sentence. Now, Hemingway -  _ Hemingway _ could end a sentence.”

“Yeah, because they were all four words long,” Rory complains.

Jess scoffs. “Gilmore, I can’t believe you don’t like Hemingway. I’m going to have to break off this friendship, I’m afraid.”

“You like Hemingway?” Paris asks him, dumbfounded.

“Jeez, don’t sound  _ too  _ surprised.”

“Excuse me, weren’t we talking about the Beats?” Rory interjects.

“We were, but now I have to give you a hard time for  _ not liking Hemingway-” _

“She’s reading Hunter Thompson for her boyfriend,” Paris says with distaste. “I wouldn’t expect much.”

“Hey!” Rory objects. 

Jess raises an eyebrow. “Is there an author you  _ do  _ like, Paris?”

“Oh, right, just because I dislike the ones you worship, I couldn’t possibly like anything e-”

Rory groans. “Stop bickering. I only have so much coffee.”

Jess laughs and hops up on the wall next to her. His arm brushes against hers, and she freezes; Jess doesn’t seem to notice, but Paris’ eyes narrow and Rory squirms under her gaze. 

“What else you got in there?” Jess asks, gesturing towards Rory’s backpack. 

“Well,  _ Fear and Loathing in Las Vegas,  _ uh... _ The Tell-Tale Heart…”  _ The corner of his mouth quirks up.  _ High Fidelity-” _

“Ooh, can I borrow that?” Jess asks. “I’ll trade you a Vonnegut for it.”

Rory gives him a wry smile. “You’ve already read that.”

“Hornby,” Paris mutters. “Acceptable.”

“Yeah, but it’s been a while,” Jess replies. “I’ll throw in  _ Howl,  _ too.”

“You write all over your books,” Rory pouts.

“Book snob,” he fires back.

Paris coughs, but it sounds an awful lot like  _ typical! _

Jess rolls his eyes. “If it’s that big of a deal, I won’t write in it. Although, you might have to confiscate all my pens.”

“No, it’s fine,” Rory says with a laugh. “I don’t mind it. Just giving you a hard time.”

He scoffs, but then he smiles and her heart skips a beat. “We can trade later?”

“Sure. Which Vonnegut do you have?”

_ “Cat’s Cradle.” _

“Ooh, that’s a good one.”

“Not half bad,” Paris admits. 

Jess grins triumphantly. “Paris Geller agreeing with me? I guess this is my lucky day.”

Paris huffs. “You know what? Forget it.”

“Oh, don’t be like that.” Jess suddenly hops down from his perch on the wall. “Can we take a rain check? Bathroom break.” He doesn’t wait for an answer and heads for the doors, slipping inside.

Paris turns back to Rory, scrutinizing her, and Rory knows exactly what she’s thinking. “Don’t say it,” Rory threatens, trying to sound as intimidating as possible. 

“Say what?” Paris asks innocently. Rory gives her a look. “Hey, you’re the one thinking it.”

“I am not thinking - I’m thinking about what  _ you’re thinking,  _ and that’s - you’re wrong.”

“And what am I thinking?”

Rory is saved from having to say anything when she hears Mr. Medina announce, “Time to get on the bus! Make sure all your luggage is in the bottom of the bus, but please, take on your smaller bags - we don’t have endless space.”

Paris immediately starts heading towards the bus. Rory hops off the wall hurriedly and zips up her bag. Jess is still in the bathroom, so she tries to wait, but one of the chaperones shepherds her towards the bus and she doesn’t have a choice but to get on. 

Rory takes a window seat near the front of the bus. She peers out the window, trying to keep an eye out for Jess. 

“This seat taken?”

Rory whips around at the sound of a very familiar voice. Tristan looms over her, arm on the top of the seat as he leans forward, almost cornering her. 

“What do you want, Tristan?” She asks dryly.

He smirks. “Nothing,  _ Mary.  _ Just wondering if this seat is taken.”

“It is, in fact.” Jess pushes past Tristan and sits down next to Rory. “Thanks for saving the seat, Gilmore.”

Rory beams. “Yeah, no problem.”

Tristan glares at the pair of them, but then someone yells at him to keep moving so he makes his way down the aisle and away from them.

“You saved me,” Rory says, relieved. “I’m considering erecting a statue of you in my front yard or something.”

Jess laughs. “No need to be drastic. A plaque will do.”

“Consider it done.” Rory shakes her head. “God, I  _ hate  _ him.”

“You’re not alone, trust me,” Jess assures her. “But I don’t want to talk about him, do you?”

“Definitely not.”

“Then it’s decided. We won’t talk about him.” Jess grins a little and Rory feels her face flush, so she quickly averts her gaze. She’d been so sure that this weekend would be fine, that she could  _ handle it,  _ but he’s been sitting next to her for a minute and her heart is already beating out of her chest. “Wanna trade now?”

“Oh, yeah, sure,” Rory replies, grateful to have something to do with her hands. 

She hands him  _ High Fidelity,  _ and he gives her his Vonnegut, but they don’t start to read. Instead, they talk, and talk, and talk. It feels natural - as natural as talking to her mom or Lane, which is a first. 

She looks out the window and sees the  _ You’re Leaving Hartford!  _ sign. The trip has officially begun.

**

(An hour into the ride, Rory falls asleep with her head on his shoulder. Jess just smiles and continues to read.)

**

“Hey, Rory,” Jess murmurs. “Wake up. We’re here.”

Rory blinks, a little bleary eyed and disoriented. “Hm?”

“We’re at the lodge.”

She rubs at her eyes, slowly sitting up. She realizes she fell asleep on his shoulder and she can feel her face heat up, but Jess doesn’t seem to mind. 

“You sleep well?” He asks, voice soft.

Rory flushes darker, but he pretends not to notice. “Yeah,” she mumbles, offering him a small smile.

“Good,” he breathes, the softest hint of a smile on his face. She follows him off the bus, only now realizing now that he’s not looking that she’d been forgetting to breathe. 

(She knows she told her mother there was no way Jess could like her, but right now, she’s starting to question it.)

The lodge is pretty nice, and it feels homey. The warmth is a relief from the cold December air outside, and as they walk in, Rory’s hand brushes against Jess’, but she thinks better of it and shoves her hand in her pocket.

The class congregates in the lobby, all chatting loudly. Mr. Medina clears his throat, trying to catch everyone’s attention. “Can everyone, er - I know that was a long bus ride, but I need you all to be-”

“Hey, everyone, shut up!” Paris yells at her classmates. The room is silent almost instantly; Mr. Medina looks quite amused, but he moves on. 

“Thank you. Now, I know everyone is very  _ excited, _ but there’s some rules and regulations that we need to lay out before you all disperse. First off, curfew is at eleven - that means in your rooms, lights off, doors closed.” 

He continues to list more rules, including, but not limited to: don’t go into a room that isn’t your own,  _ please  _ do not sneak out at night, and be careful on the slopes - “There’s a lot of paperwork to fill out if one of you gets injured,” he quips.

“Ah, now arrives the dreaded moment,” Medina says, taking something out of his pocket. “Room assignments. When you hear your name, come up here and we’ll give you a key with your room number on it.” He looks down at his list and clears his throat. “Boys first.”

She watches Jess hold his breath and then exhale in relief when they hear “Jess Mariano and Daniel Hu.” He smiles at her before going up and getting his room key. Rory smirks to herself when Medina switches to girls and she hears “Paris Geller and Rory Gilmore.”

“I told you I could do it,” Paris mutters at her as they get their keys and start up the stairs with their bags. 

Rory smiles. “I didn’t doubt it.”

“Yeah, you did.”

“Okay, I did,” she admits, “but I’m glad it worked.”

Paris grumbles something under her breath, but she’s smiling a little. 

Once they’ve put their bags away, Rory and Paris return to the lobby. Jess is sitting on a sofa and reading, but he looks up when he hears Rory call his name. 

“You two took a while,” he observes as Rory sits down next to him and Paris takes a chair. 

“That’s because Paris insisted on going over  _ ground rules,”  _ Rory explains with an eye roll. “And made me unpack.”

“You can’t just live out of the suitcase,” Paris snaps. “When was the last time you sanitized it?”

“Never?”

Paris scoffs. “You’re lucky I brought wipes so we could clean the drawers and bedspreads.”

Jess holds back a laugh. “You’re cleaning the bedspreads?”

“Hey, who knows what’s happened on these beds. Rory wouldn’t let me use my black light, so I took an extra precaution.”

Jess shakes his head. “Too many jokes...I need a moment.”

Rory nudges him lightly to reprimand him. “Are any of you gonna ski?” She asks.

“No,” Jess and Paris say in unison.

“Yeah, I figured.” Rory smiles. “How many books did we bring collectively?”

“A lot,” Jess says.

Paris snorts. “Insightful.”

“Yeah, well, you care to wager?”

“What, so I can take all your daddy’s money?”

“Ouch!”

**

When they go to bed that night, Rory discovers that Paris talks in her sleep. She smiles to herself and makes a mental note to tell Jess - although, it’s not as amusing when Rory can’t fall asleep. Eventually, though, she drifts off, only vaguely hearing Paris’ exclamation of  _ Mr. Gorbachev, tear down this wall! _

**

The next morning, Jess joins Rory for breakfast. The coffee is okay - she’s definitely had better, no doubt about it - but Jess surprises her by buying her a danish, so she doesn’t complain. 

“What is that, your third cup?” Jess laughs when Rory returns to their table with a cup of coffee.

Rory gives him a look. “I’m gonna need it if I have to put up with you all day,” she returns without any heat. 

Jess smiles and pushes his plate towards her. “You can have my last muffin, I’m not that hungry.” 

Rory thanks him eagerly and takes a bite. “So good,” she gushes, mouth full. 

“Don’t talk with your mouth full, it’s gross,” he reprimands her, but the corner of his mouth quirks up. (She tears her gaze away from his lips, knowing that staring won’t lead to any productive thoughts.)

“Jeez, you sound like Luke,” she laughs.

Jess’ brow furrows at her words. “Who’s Luke?” He asks after a moment of hesitation.

“Luke Danes. He owns this diner in Stars Hollow that my mom and I go to, like, every day,” Rory explains. “He’s a little curmudgeonly, but we like him a lot.”

“And I’m a curmudgeon?”

“You sound like one from time to time.”

Jess shakes his head. “You’re a tease, Gilmore.”

They lock eyes, and Rory feels that familiar sensation in her stomach. She looks away a moment too late and Jess clears his throat awkwardly. Rory glances at him from the corner of her eye, desperately trying not to hope. 

(Yes, things have been a little  _ different  _ lately, but she tries to tell herself she’s just overthinking it. It shouldn’t even matter - she has a boyfriend. Nothing can happen.)

**

After dinner, there’s ample time to explore. Rory finds a nature trail and drags Jess along. He protests, complaining that it’s cold, but she ignores his complaints and forces him to come along. 

“It’s actually not bad,” he admits about halfway through their walk.

Rory looks over at him in surprise. “Really?”

Jess shrugs. “Yeah. I mean, it’s cold, but...not so bad with you around.”

She blushes and ducks her head so he won’t see.

After another minute, there’s a crack of thunder above them and it suddenly begins to pour. Rory yelps in surprise, but Jess laughs, looking up at the cloudy sky.

“Some timing, huh?” He asks, still looking up.

“We’re getting drenched,” Rory complains.

“It feels nice.”

“We could catch a cold.”

Jess glances over at her with his crooked smile and her heart twinges. “A risk I’m willing to take.” With the look in his eyes, it feels like a loaded response. 

Rory swallows and regains herself. “Come on, let’s go inside.”

He hesitates before grinning. “I’ll race you.”

“Come on, we’re not six, are you really going to-” 

He takes off and she runs after him, not catching up until they’re safely inside the lodge. She doubles over, laughing, and Jess looks at her amusedly. 

“You’re too fast,” she chokes out, trying to contain her laughter.

“Years of running from the cops.”

She shakes her head. “You’re ridiculous. I’m gonna go change.”

“Wait.” She stops walking away and turns to look at him. 

“Yeah?”

He takes a step towards her. It feels like an eternity before he leans in, and she thinks he’s going to kiss her, but instead she feels him touch her hair and he pulls back with a leaf in his hand.

“It was in your hair,” he explains, voice husky.

Rory nods and swallows. “Well. I’ll see you in a few.”

“Sounds good. I should probably go change, too.”

She looks him over and he’s soaked, too. 

“Yeah.”

When she barges into the room she’s sharing with Paris, Paris looks up from her book in surprise. “What happened to you?” She demands as Rory closes the door behind her. 

Rory walks over to the dresser and takes out a sweater and some jeans. “Got caught in the rain.”

Paris snorts. “Either that or you just got baptized. Why were you out in the rain?”

“I was on a walk with Jess and it started to rain.”

Paris follows Rory as she walks to the bathroom. “You were out with Jess?”

Rory moves to close the door, but Paris stops her. “Would you let me change?” Rory asks crossly.

Paris relents and lets Rory close the door. “You were out on a walk with Jess, then?”

“That’s what I said.”

“Romantic setting.”

“Paris!”

“Hey, I’m just saying.” 

Rory opens the door, having changed into her dry set of clothes. “We are  _ not  _ having this conversation again.”

“Come  _ on,”  _ Paris groans. “You’ve been avoiding this long enough.”   
“I’m not talking about it.”

Paris grabs the hairbrush from Rory’s hand and drags her to her bed. She sits down on the one across from her. “We are talking about this, Gilmore, whether you like it or not.”

Rory glares at her. “There’s nothing to talk about!”

Paris scoffs. “How much longer are you going to deny this?”

“What am I denying, exactly?”

“You like Jess,” Paris says. “You and I both know it. Go on, tell me I’m wrong.”

Rory crosses her arms across her chest and doesn’t make eye contact.   
“I knew it! You’ve got it  _ bad  _ for him, too.”

“I don’t have it  _ bad  _ for him,” Rory argues. “It’s...I...and he, he’s just…” She trails off.

Paris sighs. “So, you have feelings for him. What’re you gonna do about it?”

“Nothing!”

“And why is that?”

“I have a boyfriend,” Rory snaps. 

Paris gives her a look. “So what? He doesn’t have to be your boyfriend if you don’t want him to be.”

“I like Dean!”

“And you like Jess,” Paris returns. “This whole will-they-won’t-they, Mulder and Scully thing is getting old. Not just for me, but for the both of you, I’m sure. And nothing is going to change unless you do something about it.”

“I’m not going to cheat on my boyfriend.”

“I’m not telling you to. All I’m saying is that I know this is wearing down on you and should look out for yourself.”

Rory fidgets uncomfortably. “What would I even say, Paris? I don’t - I have a boyfriend. Springing anything on Jess about how I feel is unfair to him. I don’t...the last thing I want to do is hurt him.”

“Figure it out, Gilmore. Make a decision. But don’t string anyone along or let someone do it to you. Gives the female sex a bad name.”

Rory sits there in silence, taking in Paris’ words. After a moment, something hits her; she feels an urge she can’t quite explain. Maybe she should act on an impulse, just this once. 

She stands up abruptly, surprising Paris. “What’re you doing?”

“I have to talk to Jess,” Rory breathes. She feels like she’s been struck by lightning - suddenly, everything is illuminated. 

“Go get him, Gilmore!”

Rory walks down the stairs, gripping the railing tightly as she rounds the corner and catches a glimpse of Jess. She almost turns and runs back up the stairs, but she holds herself back and descends the rest of the staircase, her heart beating out of her chest. 

It’s still raining, but the rain doesn’t feel that loud anymore, not really - not when she sees Jess looking out the window and the rest of the world more or less falls away. 

Jess turns around when he hears her approaching and smiles. “Hey, Rory. What’s-”

“I want you.”

Jess inhales sharply and doesn’t exhale. Rory locks eyes with him, emboldened. 

“I want to be with you, Jess, and I-” She takes a breath. “I know that this is sudden, and it’s not fair to you at all, but I just...I need you to know.” Rory pauses. “I need you to know that I want  _ you.” _

Jess blinks a couple times before he speaks, his voice a little hoarse. “Aren’t you still with Dean?”

Rory attempts to ignore the growing sinking feeling she feels as the seconds pass. “Unless you can give me a reason not to be,” she murmurs after a moment. 

Jess stares at her, completely speechless. His mouth is still parted, as if he wants to speak, but he stands completely still and doesn’t say a word.

“Things are...it’s better with you, Jess, than it is with anyone else. And I...I feel  _ warm  _ when I’m with you. Like, I’m...like when we were ice skating, and I just  _ knew  _ that everything I’d been feeling ever since I met you was...more. And I just...I want  _ you.  _ And I thought that maybe...that you might…”

He’s quiet, frozen, his chest rising and falling with his breaths being the only sign of life. 

She can feel her eyes filling with tears, but she fights the urge to cry, her voice wavering with the effort. “It can’t just be all in my head, right?” Rory asks, her voice small. “Jess?”

Rory searches his eyes for any sign of reciprocation, anything at all, but he’s unreadable, like he always is and  _ god  _ she was an idiot, thinking he might actually return her feelings. 

“Fine. I just...I guess I was wrong, then,” she says, blinking back tears.

“I…” Jess trails off, unable to say anything more.   
“Okay. Okay, well, I, uh...I guess that’s it, then.” Rory turns around and wipes at her eyes furiously, beginning to walk away from him. 

“Rory-”

“No, no, just...leave me alone,” Rory chokes out. She hurries away from him, and once she rounds the corner, she starts to cry. 

Rory holds a hand over her mouth to conceal her sobs, feeling like everything is crashing down around her, and everything gets infinitely worse when she hears footsteps behind her and she turns around to see Tristan.

“Go away, Tristan,” she chokes out, trying to run, but he steps in front of her and doesn’t let her leave. “What’s wrong, Mary?” He asks, head cocked to the side.

She shakes her head. “Nothing.”

“It’s obviously not nothing,” he chortles, looking way more amused than he ever has the right to. “Is this about a guy?”

“It’s none of your business!”

“Was it Jess?” He questions. “Don’t tell me my stepbrother did something to hurt you.”

Rory stops trying to get past him and freezes, eyes wide. “What?”

Tristan’s brow furrows in mock concern. “Didn’t he tell you? Jess is my stepbrother.”

Rory blinks at him, utterly dumbfounded. “He...he didn’t.”

“Oh. Well…” Tristan  _ tsks.  _ “Had to find out eventually, right? Just too bad it wasn’t from him,” he adds, but he doesn’t sound remorseful at all.

“Just leave me alone,” Rory sobs. She pushes past Tristan and runs away from him, thankful when he doesn’t follow.

Rory finds herself back in the lobby, but Jess is gone. She’s completely alone.

She collapses on the ground and cries, her heart breaking in two. 


	17. The Long Winter

**Summary for the Chapter:**

> Rory deals with the aftermath of the ski lodge trip.

**Notes for the Chapter:**

> Thank you guys for being patient with these slower than usual updates! Unfortunately, thats's going to continue to be the case for a little bit - I've got some big tests and assignments coming up that I need to prioritize, so I really should set the writing aside until Monday at the earliest. I'll try to update as soon as I can, but I just wanted to update you all.  
> In any case, I hope you enjoy this chapter!

It’s past curfew when Mr. Medina finds Rory crying in the lobby. She hasn’t moved for god knows how long, and she starts to apologize, ready for the worst, but he won’t have any of it. Mr. Medina simply leads her to her room and says goodnight, no questions asked. 

Attempting not to wake Paris, Rory climbs into bed still wearing her clothes. She pulls the covers up to her chest and squeezes her eyes shut, willing away the tears that are threatening to spill. She’s cried over him enough tonight.

She falls into a deep, dreamless sleep, far away from any thoughts of Jess. 

**

“Okay, what the hell happened to you?” Paris demands the next morning.

Rory shoves her bag in the compartment under the bus with more force than required; she’s admittedly very grumpy this morning, but she’s not about to admit the real reason why. “What do you mean?” 

“You look terrible.”

“Gee, thanks,” Rory grumbles. She kicks her suitcase deeper into the compartment for good measure. Of course, she _knows_ what Paris means - she caught a glimpse of herself in the mirror while getting dressed and her eyes are red and puffy and she has a horrible headache to boot.

“Seriously, what’s going on?”

“I don’t want to talk about it.”

“C’mon, Gilmore. You can stop pouting and just talk to me.”

“No,” Rory says, more firmly this time. “I’m not talking about it, end of story. Got it?”

Paris eyes her skeptically but drops it. “I’ll save you a spot,” she says, glancing behind Rory at something before turning and boarding the bus. 

Rory grumbles under her breath, turning away from the bus, but she isn’t looking where she’s going so she collides headfirst into someone almost immediately. 

“Sorry, sorry, I-” She starts to apologize frantically, but then she sees who she ran into and her stomach drops forty flights and she doesn’t feel apologetic so much as embarrassed. 

Jess blinks in surprise, caught off guard. After an entire morning of avoiding eye contact and leaving the room if the other was there, she barrels right into him and makes everything a million times worse. Great.

“It’s fine,” he says, still looking surprised. 

It’s quiet for a moment before she speaks again. “I gotta go,” she mutters, trying to move past him, but he reaches out and stops her, like it’s a reflex, his brow furrowed.

“Wait.”

She glares at him. “No.”

“Rory.”

“No!” Rory exclaims again. She hurries away from him, but he takes her wrist - not too tight, but firm - and stops her again.

“Rory, please, I just want to talk.” 

“What? What do you want to talk about?” She demands, whirling around to face him. “After everything that happened, you just want to _talk?”_

Jess anxiously looks around them. “Yeah.”

“You don’t get to talk, Jess,” Rory snaps. “Not after last night.”

Jess looks at her, a little helpless. “Rory.”

“You don’t get to say anything,” she says again, straightening up and locking eyes with him. “This can’t be fixed with an apology. This is on you.”

“What exactly did I do?” Jess asks her.

“Are you seriously asking me that?”

He shrugs.

“Fine,” Rory snaps. “You want to know what you did? You let me totally make a fool of myself last night, Jess, that’s what you did.”

Jess raises an eyebrow. “So that was my fault?”

“Yes, it’s your fault!”

“And how do you figure that?”

She glares at him. “You led me on. You made me think that - you made me think that you felt something for me, I guess, but you don’t. And maybe that’s on me, for falling for everything - all the leaning in close and touching my hand and - why would you do that? Why?” Jess swallows, pain etched in his face. “What could you possibly gain from that?”

Jess stays silent, the look on his face eerily familiar to how he looked at her the night before. 

“I was telling you something really personal and important and you just _stood_ there, staring at me like I was an alien, letting me go on and on and on without saying a _word._ If you have an excuse for that, I’d _love_ to hear it, because honestly? I’m curious to see what you can come up with.”

His eyes narrow. “And I take all the blame. For _your_ decisions. That’s very accusatory of you, Gilmore.”

“Are you-” She huffs. “Maybe it’s on me, then, for falling for all the cliches and the stereotypes, but I don’t think that’s fair. I told you I liked you, Jess, and you just-”

“What did you want me to say?” Jess hisses. “You have a _boyfriend,_ Rory, and one that you’re pretty fond of, by the way. I don’t know what he’d have to say about all this, but I’m guessing he wouldn’t be very thrilled.”

Rory scoffs, momentarily at a loss for words. “This isn’t about Dean, he’s-”

“It _is_ about Dean! You’re angry at me for, what, not jumping up and down with glee when you told me you _wanted_ me, but what would you have wanted me to do?”

“You could’ve said _something,”_ Rory retorts, _“anything,_ rather than let me go on like an idiot and embarrass myself even more-”

“I’m not responsible for your actions, Rory,” Jess growls. “What you did - that’s all on you. You can’t pin that on me. You know, you’ve been going on and on about how I’m such a horrible guy and how it’s all my fault, but you’re not all that innocent, either.”

“How can you try to turn this around on me?” 

“I get that no one in your perfect little town has ever held you accountable for your actions,” he sneers, “but news flash, Rory, wake up - you’re not perfect. Maybe everyone told you you are, but you’re not. So you can mope and pout and accuse me all you want, but at the end of the day, but this - it all falling apart - that traces back to you.”

“I can’t believe I told you I liked you,” she muttered. “No, actually, I can’t believe I-”

“You can’t believe you liked me?” Jess scoffs. “You said...you said it was better with me than with anyone else, and that includes your precious boyfriend, I’m pretty sure. And that’s nice, that’s very nice, but I don’t want to hear that. I can’t just be the guy you go to as a last resort.”

“Was it all a game, Jess?” She asks, deflecting. “Trying to charm me, shake me up, make me fall for you? Well, good job. You did it.”

“I didn’t-”

“Was any of it real? Or was it just part of your rivalry with Tristan, your _stepbrother?”_ Jess’ widen and Rory feels some sick kind of satisfaction. “Yeah. I know. And you know what the worst part of it is? I had to hear it from him.”

“Rory…” He trails off, his tone desperate. 

“I trusted you. I relied on you. I confided in you. You had _months_ to tell me, but you didn’t. So, whatever. You win. You can go rub it in his face, now, that you beat him to it. You got the girl to fall for you. Congratulations.”

“You think I saw you as some kind of prize to be won?”

“Yeah, I do,” she says coldly, holding her head up high. 

“Then you’re a lot less intelligent than I thought you were.”

Rory almost flinches at his sharp tone. “Sucks, doesn’t it, things turning out to be different than you thought they were?”

“Hey, don’t-” He cuts himself off, fighting to keep himself composed. “That’s not fair,” he says helplessly.

“A lot of things aren’t fair!” Rory exclaims. “But I don’t want to hear it, Jess, I don’t. God, I can’t believe we were friends. So go _home,_ Jess, to your big fancy mansion and your stepbrother and your stepfather and your _mom.”_

Jess flinches. His mouth is parted, trying to fathom out a response, and he’s blinking a lot more than usual. “Why did things have to change, Rory? We were doing good. What we had - it _worked._ You...you were my best friend.”

“Yeah, well, maybe I wanted to be more than that.”

Jess doesn’t reply right away, swallowing again and fighting to keep his composure. “The town princess can’t always get what she wants,” he says cooly.

“You’re just like Tristan,” she says. He flinches again “Everything is just a game to you, isn’t it? And you know what? I don’t care. Because I am done. You, me, anything that was ever there at all - I’m done.” 

Jess bites his lip and doesn’t meet her eyes. 

“I’m done.”

She turns on her heel and boards the bus, leaving him in the dust.

She slides into the seat next to Paris, who is already looking queasy. 

“How’d it go with Jess?”

Rory sets her bag down by her feet. Jess passes by them, his gaze lingering for a little too long. “It’s all just...over.”

Paris doesn’t ask for clarification as they pull out of the parking lot and leave the lodge behind.

**

“God, I am _exhausted,”_ Lorelai complains, dragging Rory’s suitcase over the threshold and kicking the door closed behind her. “I was up all night listening to Babette and Maury singing to their cat.”

“You’re not the only one who didn’t sleep well,” Rory grumbles. She drops her backpack onto the ground, relishing in the loud _thud_ it makes against the wood floor. 

“Okay, what is up with you?” Lorelai demands, eyeing Rory’s backpack warily. “You barely said a word the entire ride home, and now you’re all... _grouchy.”_

Rory scrunches her nose. “I am not _grouchy.”_

“Yes, you are. You’re green, furry, and you smell like a trash can.”

“You’re a riot. Go into comedy, maybe they’ll give you the recognition you _don’t_ deserve,” Rory grumbles, kicking her bag into her room.

“Hey, this isn’t cool,” Lorelai says harshly. “I get that something is going on, whatever it may be - teenage angst or a really bad book - but you don’t get to take it out on me.”

Rory glares at her mom. “Fine.”

Lorelai watches Rory as she throws her things into her room, looking concerned. “You’ve got some voicemails, by the way, from Dean.”

Rory checks the answering machine and sure enough, there are ten messages. She purses her lips together and starts listening.

The first one is fine, just _hey, it’s Dean, checking in to say I miss you._ She doesn’t smile, not like she would have three months ago, but instead moves onto the next one.

It’s angrier, right off the bat. He sounds harsh, and pissed, and suddenly her palms are a little sweaty and she feels like she wants to cry. _I can’t believe you went on this trip. I told you I didn’t want you to go, but I guess I’m not important enough to you, am I? Go off and have fun with Jess, I guess._

The rest range from calm to angry back to calm again. Once she’s listened to them all, Rory simply stands there, gripping the edge of the table so tight that her knuckles turn white.

It’s silent for a moment before she hears her mother approaching. Lorelai reaches over and erases the machine, concern and worry etched deep in her face. She doesn’t say a word.

Rory pushes past her and into her room, slamming the door shut behind her. She wipes away her tears angrily - everything feels like it’s falling apart. Or, rather, everything already did. Her friendship with Jess is just _gone,_ crumbled in the blink of an eye. She’s not sure if she really believes the things she said to him, but she’s still angry at him for not feeling the same way, for keeping his secret about Tristan, for making her want him _so much._

But most of all - and this she knows - she’s angriest with herself for throwing it all away. 

**

The next two weeks move by slowly. 

Rory doesn’t do much, really, and that includes speaking to her mom - she knows that it’s wrong of her to give her mom the cold shoulder, but if they start talking, the subject of Jess is going to come up, and Rory really doesn’t want to be lectured.

She spends her winter break mostly in the library, hidden away in that corner she’s monopolized ever since she was a kid, pouring over book over book, trying desperately to not think about _him._ She spends time with Dean, too, he wouldn’t have it any other way - but _Battlebots_ ends up feeling pretty old and she’s tired of reassuring him that she would much rather be here with him than with Jess.

(She _hates_ lying to Dean, she really hates it, but she supposes she’s been lying this whole time. The truth is, she wishes she could talk to Jess more than anyone right now. And it’s tearing her up inside.)

Despite the uneventfulness of her break, by the end of it, Rory is exhausted. No amount of Nico or Elvis Costello is going to soothe her nerves about seeing Jess again when she goes back to school, and those thoughts plague her constantly throughout her two weeks off. 

But as it turns out, she doesn’t even need to worry.

**

The first day back, Jess isn’t waiting for her outside. Whatever, it’s not like she expected him to, not after what happened between them at the ski lodge, but she starts to worry when he’s not in the halls as she walks in. He’s not there for first, second, or third period, and he doesn’t show up at lunch, either. In fact, she doesn’t see him at all.

 _(Maybe it’s another family thing,_ she thinks to herself, suddenly regretting mentioning them during their argument. _Maybe that’s it and he’ll be back tomorrow and it’s all fine.)_

**

Jess isn’t there the next day, either.

**

The third day after break, Jess is absent yet again, and Rory is really starting to worry. She’s considered calling him, but doubts he’d pick up, so she doesn’t. She’s angry, yes, she wants to hate him, but he’s still important. It’s as simple as that.

At the end of the school day, Rory knocks on Mr. Medina’s door.

“Come in,” he calls from the other side.

Rory slips inside the classroom and closes the door behind her. “Hey, Mr. Medina.”

He looks up from his desk and smiles in surprise. “Miss Gilmore, hello. What brings you here? Everything okay?”

“Yeah. I, uh, I had a question,” she confesses, “but actually, now that I think of it, it’s not really that important, so I’ll just-”

“If you have a question, it’s perfectly fine,” Mr. Medina says with a chuckle. “Come on, why don’t you sit down? Don’t get me wrong, I don’t mind shouting across the room, but it might be a little easier.”

Rory smiles despite herself and pulls up a chair. “I wanted to ask about Jess,” she blurts before she can lose her nerve.

Mr. Medina raises his eyebrows in surprise. “What about him?”

“Well, he...he hasn’t been here the past few days, and I just…” She trails off. “Do you have any idea what happened to him?”

Mr. Medina grimaces slightly. “Mr. Mariano is dealing with some, er... _family issues_ at the moment. He’s taking some time off from Chilton.”

Rory blinks a couple times, trying to work out a response. “Do you know where he is?” She finally asks.   
Mr. Medina gives her a smile - a sad one. “He’s fine,” he says. “Rory...I hate to bring it up, but...are you doing alright? I didn’t want to pry, as it’s none of my business, but after the ski lodge trip…”   
“I’m…” Rory swallows and looks down at her lap. “There’s just...a lot going on right now.”

He nods in understanding. “Forgive me if I’m overstepping, but...I say you should talk to your mother about this.” Pause. “She...she usually knows how to handle...well, whatever this is about.”

“I know,” Rory admits. “Just…” She shakes her head. “I’m really worried about him.”

“He’s okay,” Mr. Medina says firmly. “I’m sure you’ll see him soon.”

Rory gives him a grateful smile. “Thank you, Mr. Medina. I’m sorry for...everything, really, but I appreciate this.”

“Anytime.”

She glances over at the door. “I’m gonna…”

He nods. “Okay. Have a good day, Miss Gilmore. And I wouldn’t worry too much about Mr. Mariano. Something tells me it’ll all work itself out soon enough.”

**

(She doesn’t agree with Mr. Medina, really, but she keeps that to herself.)

**

“Okay, trip to the video store or should we try to find something in our collection?” Lorelai asks that evening, sitting down on the couch. “Taylor’s not letting them rent out any movies with Tom Cruise or Bruce Willis for some reason, but if I bribe Kirk I think I can get us one of the Die Ha-”

“Mom,” Rory says, sounding way too desperate to her ears. Lorelai perks up with concern, her brow furrowed. “Mom, I...I need to tell you something.” 

“Okay,” Lorelai replies slowly, frowning. “Is this ‘Mom, I’m pregnant’ bad or ‘Mom, I accidentally got involved with a street gang and was forced to rob a bank and things got out of hand so can you please help me hide this body’ bad?”

“Neither.” Rory takes a seat next to her mom on the couch, anxiously pulling her sweater over her hands repeatedly. “I just…” She swallows. “I am _so_ sorry for how I’ve been treating you these past few weeks. It was so unfair of me, and I shouldn’t have acted like that, and I _hated_ it the whole time, I did, I swear, but I knew that if we talked we’d end up talking about what happened at the ski lodge and I really, _really_ didn’t want to talk about it.” She takes a breath. “Please forgive me.”

Lorelai rubs her daughter’s arm reassuringly. “Thank you. But talk to me now, please - what happened up there?” (There’s a nervous edge to her voice that almost makes Rory want to _laugh.)_

Rory squeezes her eyes shut. “I messed up with Jess, mom. I really messed up with him.”

Lorelai doesn’t say anything, but she strokes Rory’s cheek for a moment before pulling her hand back.

“I didn’t plan on it, but we’d gotten caught in the rain and with the way he was looking at me I just thought…” She swallows. “So I told him...I told him...I told him how I felt. I told him I wanted him,” Rory says with a deep sigh. “And he...he just stood there, staring at me, not saying a word - oh, no, that’s right, he _did_ say something. He said ‘aren’t you still with Dean?’ And I know he had a point, but that’s _it._ That’s all he said.”

“That must hurt.”

Rory nods. “It does. It does, and it shouldn’t, but it does, and he - god, I just can’t believe that I fell for him in the first place. He led me on, making me think that all his glances and the hand holding and getting real close meant something, but I guess it didn’t.”

“Rory, honey, maybe…” Lorelai trails off and then shakes her head. “Nevermind. Go on.”  
“What?” Rory asks, bewildered. “What are you thinking?”   
“I’m thinking…” Lorelai sighs. “I’m thinking that maybe there’s more to Jess’...Marcel Marceau impression than you might think there is.”

“Like what?”

Lorelai hesitates. “Well...it is a lot to spring on him at once. And I’m not blaming you, it’s not like you’ve had an excellent role model when it comes to functioning relationships, but...maybe he was just caught off guard.”

“But I _know_ Jess,” Rory says miserably, “and he wouldn’t do that to me if he really felt that way. I feel so _stupid.”_ Her voice cracks on the word _stupid._ “He played me. And I let him.”

“Rory…”

“I fell for him, Mom, hard. And I tried, I tried to see if he felt the same way, but...he doesn’t want me. That’s what it comes down to. He just doesn’t want me.”

“Oh, babe…”

“You know what makes it even worse?” Rory asks, her voice fragile. “Tristan is his stepbrother. That’s why they hate each other, why they’ve been at each other’s throats this whole year, and Jess never even told me. I had to find out from Tristan. Jess couldn’t even tell me,” she repeats.

Lorelai smooths down Rory’s hair comfortingly. “God, that’s rough.”

“So why did I do this? Why did I mess everything up? We got into a fight the next morning, and he hasn’t been at school since we got back, and I just...I wrecked everything.”

“It happens.”

“You’re not going to lecture me?”

Lorelai sighs. “I...look. Yes, you didn’t make a great decision, but...it was just...a moment of weakness,” she suggests finally. “We’ve all had those before, and we’ll all have more. It’s just a part of life.”

“Like what?” Rory asks with a sniff. 

Lorelai cringes. “Oh, nothing, just the _brilliant_ idea I had to go to a certain English teacher’s apartment in Hartford this afternoon.”

Rory’s eyes widen. “You didn’t.”

“Oh, but I did.” Lorelai laughs under her breath. “Yep. I just...drove over there after work and knocked on the door. Nothing happened, though, don’t worry. I don’t even know what I wanted, but it doesn’t matter, because he wouldn’t even let me in. Something about having a friend crashing on his couch, I don’t know.”

Rory thinks about her conversation with Mr. Medina earlier that day, unsure of what happened between that and her mom’s impromptu visit. “Weird.”

“Yep,” Lorelai agrees. “But, like I said, it was just a moment of weakness.”

“A moment of weakness,” Rory repeats. 

Her mom gives her a sympathetic smile. “It’s gonna be okay.”

“You think?”

“I do,” Lorelai says firmly. “It’s gonna suck for a while. But eventually, it’s all going to be okay.”

Rory nods, but she doesn’t think she believes her mom at all.

**

Luke is closing up alone tonight. Caesar went home early, citing a headache that Luke _has_ to believe because Kirk took an hour longer than usual to order his dinner. He doesn’t mind it, really - it may take him a little longer to wipe down tables and put up the chairs, but it gives him time to think.

About halfway through his routine, Luke is startled out of skin by a knock at the door. At first he assumes it’s Lorelai (who else would knock on his door at ten at night?) but then he moves closer to the door and he realizes it’s most definitely _not_ Lorelai.

It’s _Jess._

Surprised, Luke unlocks the door and steps over the threshold. He only saw his nephew a month or so ago when Mr. Dugray (he _insists_ that you call him Mr. Dugray) was this close to kicking Jess out again over a little prank and Luke had to do damage control.

But here Jess is, standing before him with nothing but a duffle bag slung over his shoulder. Luke frowns, formulating what to say. 

He settles on asking, “Jess?” 

It’s silent for a moment as Jess seems to work up the courage to open his mouth. 

“You got an extra couch for me to crash on?”


	18. The Little Prince

**Summary for the Chapter:**

> After his fallout with Rory, Jess finds himself reevaluating everything.

**Notes for the Chapter:**

> It's been a while! I want to apologize for this more or less impromptu three week hiatus. I have a lot of work to do for my classes and met a bitch of a writer's block, but I managed to get this chapter done over the last few weeks, and finally, it's more or less ready to be posted.  
> Thank you guys for all your patience!

Jess sits in the emergency room, gripping the armrest so hard his knuckles turn white. He’s unsure of how long he’s been sitting here - a minute, an hour, a month maybe. Even the people sitting around him or milling about the waiting room fail to keep him grounded. He can’t get the image out of his head - his mother, on the bathroom floor - and he shudders involuntarily, wanting to be anywhere else but his own skin. 

He knows that he’s probably better off without her, and that his life was never made any easier with her in it, but no matter how much he tells himself this, there’s a part of him that refuses to believe it. Jess squeezes his eyes shut, hell bent on at least staying composed. 

Even if his entire life has been uprooted tonight, changed in the blink of an eye, he can stay afloat even if he feels like he’s drowning. He’s known this his whole life.

So why does it suddenly feel like a lie?

**

Liz Danes always said that she had a good kid. 

When Jess was reading four years above his grade level, she’d gush to the other mothers about how  _ smart _ her son was and that he was just  _ such _ a good kid. And it wasn’t  _ not  _ true - he was good. Good until he wasn’t.

Jess was eleven years old when he got suspended for the first time. When Liz came rushing into the principal’s office, an hour late and hungover, and demanded to know what happened, all he would say was, “it wasn’t my fault.”

He still remembers the haranguing he got that night, her words sharper than a knife. 

Jess was thirteen when he got suspended for the second time. Liz dragged herself to the principal’s office after a morning of the cheapest beer she could find at the nearest bodega and asked Jess what happened. He said, “he had it coming, okay?” And he left it at that. 

Jess was fourteen when he got kicked out of school for the first time. Liz didn’t bother to pick him up - he took the subway home, the contents of his locker shoved in his bag. 

After a childhood full of harsh words from his mother and a new guy around practically every year, nothing could faze him anymore. So when his mother met a rich divorcé from Hartford, Jess didn’t blink twice. He assumed with his mother’s track record that the relationship would all be done and over with within a year at the most. He held onto this mindset even when they got married - that had happened before, it would happen again. 

But the move to Hartford is what shook him.

Jess had lived in New York his whole life. He knew the city like the back of his own hand, and he never expected Liz to uproot their lives and move them into Hartford high society, which was like a whole other planet. But he went along with it, didn’t put up a fight, and he  _ made do. _

Until, that is, when his mother died. 

His mother died, and then Jess was forced into ties tied so tight he couldn’t breathe and blazers that were just a little too big and classes that he hated, all without an ounce of sympathy from anyone. He was thrust into high society and an elite private school, two places he could never fit into. 

And then - then he met Rory Gilmore. He met Rory Gilmore, and suddenly, everything changed. He actually started to look forward to school, believe it or not; he completed assignments and actually  _ tried;  _ damn, he even went to school events for her, knowing even then that his feelings wouldn’t be reciprocated. 

After her birthday party, Jess was pretty sure he was completely in love with her. And even though she only saw him as a friend, he knew he could live with that. She was in his life, and that was enough; actually having a reason to get up in the morning and to look forward to things and to  _ just keep moving  _ was more than he would’ve ever expected to have. 

He should’ve realized, though, that losing her - that was always in the cards.

**

“I want you.”

Jess inhales sharply and his breath catches in his chest. His blood goes cold at her words, completely catching him off guard. 

“I want to be with you, Jess, and I - I know that this is sudden, and it’s not fair to you at all, but I just...I need you to know. I need you to know that I want  _ you.” _

Jess searches her eyes, trying to find something to hold onto to keep him grounded, but all he can feel is  _ fear _ and all he can think are second thoughts. “Aren’t you still with Dean?” He asks tentatively.

Rory hesitates. When she finally speaks, her voice is soft and timid, but her words still cut like a knife. “Unless you can give me a reason not to be.”

Jess tries to speak, to say  _ anything  _ at all, but it’s like his voice is gone. He knows, he knows this is all he’s wanted and dreamed about for the past few months, but now that it’s here, now that the moment is  _ real,  _ he’s too afraid. He’s too afraid to say a single word. 

(She’s still with Dean. She’s still with Dean, and he cannot be that guy, not with her. Not when it’s Rory.)

She continues to speak, breaking Jess’ heart even more in the process. “Things are...it’s better with you, Jess, than it is with anyone else. And I...I feel  _ warm  _ when I’m with you. Like, I’m...like when we were ice skating, and I just  _ knew  _ that everything I’d been feeling ever since I met you was...more. And I just...I want  _ you.  _ And I thought that maybe...that you might…”

He still can’t find his words. And besides, even if he said what he wants to say, he’s not sure she would believe him.

“It can’t just be all in my head, right?” Rory pleads. “Jess?”

His heart is slowly breaking in his chest as he watches her. Inside, he’s screaming at himself to  _ just say it, _ but he can’t _.  _ He can’t cross that line. He’s been conditioned not to. 

Rory looks a little surprised as she blinks back tears, taking a little step back from him. “Fine. I just...I guess I was wrong, then.” 

“I…” is all he can choke out.

“Okay. Okay, well, I, uh...I guess that’s it, then.” She turns and walks away from him, and Jess’ heart seizes in panic. 

His body acts of its own accord and he takes a step to go after, reaches out - “Rory-”

“No, no, just...leave me alone,” she chokes out before she slips out of his sight. 

For a split second, Jess almost  _ laughs.  _ Of course. Of course, he had to fuck up the only good thing in his life. He had to go and lose the person he cares about the most in the worst way possible, hurting her in the process. 

Jess allows himself a moment before he swallows and goes up the stairs, ignoring the urge he has to break down and cry. He ignores his roommate’s questions when he enters their room and shuts the door behind him, grabbing a t-shirt and sweatpants and going into the bathroom to change. Daniel’s a nice enough guy, but Jess isn’t, and right now, he doesn’t really care about that at all. 

He lays in bed, staring at the ceiling, full of regret. He barely gets an hour of sleep. 

**

The next morning, Jess doesn’t feel any better at all. He slowly gets dressed and heads down to breakfast, tuning out whatever Daniel is saying about The Cure. 

Toast isn’t much of a breakfast, but it’s all he can stomach right now.

Rory and Paris sit down at a table near them and he can’t help but look. His heart breaks just a little bit more when he notices that Rory looks like she’s been crying all night. 

She catches him looking and he diverts his gaze immediately, deciding to focus on spreading butter on his toast. When he looks up again, she looks away quickly and makes a point of it to start up a conversation with Paris. 

He doesn’t see her again until an hour later when it’s about time to board the bus. Students congregate in the lobby with their luggage, a few getting a headstart and going to the bus to try to get a good seat. 

He takes a seat in one of the armchairs, about to grab a book from his back, but then he sees Rory descending the stairs. Jess immediately stands up, grabs his bag, and leaves the lobby, feeling her eyes fixed on his retreating figure. 

**

Jess feels numb as he gets off the bus and grabs his duffel bag and slings it over his shoulder. Rory pushes past him, making her way towards a Jeep parked right outside the iron gates. He watches it drive off, feeling an odd heaviness in his chest that he can’t quite determine the root of. 

He’s still a little angry, but he swallows his resentment down and knows that she’s right, there’s no use in fighting it - it’s all over. Whatever there may have been between them, it doesn’t matter anymore. It’s over.

“Dad sent us a car,” Tristan says, walking up next to Jess and shaking him out of his reverie. 

“Great,” Jess mutters. He kicks at some pebbles by his feet for a lack of anything better to do.

A limousine pulls up a few minutes later and a man in a suit gets out. “Dugray?” He asks. Jess nods, but his skin crawls at the thought of being a  _ Dugray.  _

Jess climbs in after Tristan and the driver closes the door behind him. Tristan immediately opens a compartment, revealing bottles of alcohol. “Want one?” He asks.

Jess glances towards the bottles. “No, thanks,” he replies stiffly. The sight of the bottles are making his stomach turn, so he looks away and out the window instead, watching Hartford pass by them. 

It’s silent for a few minutes before Tristan speaks again. “You have a good trip, Jess?” He asks condescendingly.

Jess scoffs. “Sure. Why not.”

Tristan raises an eyebrow. “Are you angry about something?”

Jess gives him a cold look. “What do you think?”

“I’d say yes, but I’m having some issues figuring out  _ why.” _

Jess takes a breath to steady himself. “You don’t have any educated guesses? How much  _ did  _ your father bribe Charleston to get you into Chilton?”

Tristan glares at him. “Careful, Jess.”

“Where do you get off on being such a fucking dick?” Jess growls. 

“Woah!” Tristan exclaims mockingly. “That was a little uncalled for.”

“No, it wasn’t,” Jess spits. “You told Rory we were step brothers? Are you kidding me?”

“It’s not my fault you didn’t tell her,” Tristan replies with a shrug. “She would’ve found out sooner or later.”

“She should’ve heard it from me.”   
“You had all the time in the world to tell her!” Tristan exclaims. “You forfeit the right to be upset.”

Jess scoffs. “You did this all on purpose, didn’t you? You  _ knew  _ she’d be upset that I didn’t tell her, and that it would just…” He trails off.

“Do what, Jess? Do what? Because from where I’m sitting, you did all the damage yourself that night. I assume she was crying because of you.”

Jess’ jaw clenches tight. “You told her after…”

“Based on that bitch fight I caught a glimpse of between you two,  _ you  _ were the one that ruined things with her. I was simply doing her a favor and letting her know the truth.”   
“Bullshit,” Jess snaps. “You don’t give a shit about Rory or her wellbeing. If you did, you’d leave her alone.”

Tristan glares at him. “You’re one to talk. Let’s examine why, shall we? From what I heard from the two of you,  _ you  _ hurt her, not the other way around. You follow her around like a lovesick puppy for  _ months,  _ and then just leave her hanging. What was it, the thrill of the chase?”

“Oh, and you wouldn’t do that, right?” Jess growls, blood boiling. “Because you’re just so much better than me?”

“You don’t belong with Rory,” Tristan spits. “You never did. You’re not good enough for her, Jess, and you  _ know  _ it. That’s why you didn’t say anything, right? You knew that you’re not worth it, that she’d be wasting her time on you.”

“All I know is that you don’t know anything about me  _ or  _ Rory,” Jess says, as evenly as he can. “And I know that you crossed a line, telling her about us being step brothers, because you only did it to sabotage my relationship with her.”

“So what if I did?” Tristan smirks. “If all it took was a few words from me to ruin your relationship, how much of a relationship was there to begin with? And besides, let’s face it, Jess. Everyone’s better off without you. I know your mother told you as much before she fucked off and  _ died.  _ I would’ve done the same if  _ I  _ was your mother.”

Jess inhales deeply and exhales slowly. For all the wear and tear he’s been through, firing back with equally hurtful things isn’t worth it. It’s not.  _ You still have to live with him,  _ Jess reminds himself. “You know, now that I think about it, you  _ do  _ look an awful lot like Mrs. Doubtfire.”

“I don’t know what Rory saw in you,” Tristan continues, unfazed. “Maybe you two deserve each other, after all. I mean, she must be pretty idiotic to want  _ you.  _ It’s good, I guess, that that little princess didn’t get what she wanted this time. She was getting pretty spoiled with that jackass from the dance, anyway...not sure if I want your sloppy seconds.”

“Watch it,” Jess warns.

“What’re you gonna do?” Tristan snorts. “Hit me? Take me down in this limo? C’mon, Jess, is it really worth it getting  _ this  _ worked up over a girl like  _ tha-” _

He doesn’t get the chance to finish his sentence, because Jess grabs his arm and twists it behind him. Tristan cries out in pain, trying to get out of Jess’ ironclad hold.

“Talk about Rory like that again and I’ll do worse,” Jess growls. “I don’t care if you’re upset that she doesn’t want you, and you can bitch about me all you want, but you do  _ not  _ get to talk about her like that. Understand?”

“I-”

_ “Understand?”  _ Jess asks more forcefully.

“Y-yeah…” Tristan trails off, looking shocked. 

Jess lets go, and Tristan rubs his arm, staring at Jess with a gobsmacked expression. Far from satisfied, leans back in his seat and pulls his book out of his back pocket. He leans back to read, but can’t find it in him to focus the entire way to the house.

**

When the limo pulls up to the Dugray mansion, Tristan goes right inside and leaves his bag behind for the driver to take up. Jess ignores the driver’s offer to take his bag too, and instead grabs his duffel and drags it inside himself.

Jess goes straight up the stairs to his bedroom and slams the door shut. He drops his bag at his feet and stares at his bedroom. He’s suffocating. This room and this house and this world - he can’t breathe. He misses New York desperately and hates his mother for taking him away from the city he’d called  _ home  _ his entire life and leaving him stuck in a place that makes him feel like this. 

Rory’s words from earlier are sticking with him now, he can’t get them out of his head -  _ so go home, Jess, to your big fancy mansion and your stepbrother and your stepfather and your mom. _

This isn’t home. It was never home.

He needs to get out. 

Jess falls back onto his bed and stares at the ceiling. For the first time all day, he’s truly alone with his thoughts. He wants more than anything to see Rory - no, he  _ needs  _ her, needs to see her and talk to her and just  _ be  _ with her - but he can’t. He forfeited that privilege when he let her run away crying, breaking her heart and his own in the process.

He sits up and wipes at his eyes furiously before he breaks down, stubbornly swallowing down the lump in his throat. He’s never needed anyone before, not like this. He’s never felt like this ever, like losing someone is losing a piece of yourself, a pain so agonizing that it hurts more than anything he’s ever experienced.

Jess can’t tell if the thought of her is hurtful or healing - maybe a little bit of both - but he takes a breath and forces himself to get his head on straight. He can’t stay. That’s all he’s certain of right now. He needs to get out.

**

A week passes by. Jess spends most of his time in the library, the only place in this house he can stand; he pores over book after book, letting himself escape, at least for a little while. 

In retrospect, he could’ve gotten out easier, made a much cleaner break, but those sorts of things only occur to him when he’s already out the door. No going back, no undoing - just keep moving forward.

Jess sits at the dining table, staring down at his food. Normally, he likes the steak that the cook makes just fine, but tonight, he doesn’t have the stomach for it.

“Pass the salt.”

Jess takes the salt shaker and pushes it towards his stepfather, watching it slide across the smooth surface. 

His stepfather grabs the shaker and glares at Jess. “You shouldn’t do it like that. You could scratch the table.” 

Tristan snickers into his food.    
Jess mutters under his breath and angrily stabs at his steak with his fork. Family dinners such as this are some personal sort of torment. Most nights, he can avoid them by claiming he has homework or simply by just not showing up, but tonight, his stepfather wouldn’t have it.

His stepfather’s eyes narrow. “What did you say?”

“Nothing.”

“No, you muttered something. What was it?”

Jess tries to stay calm. “Like I said, it was nothing.” He glances over at Tristan, who looks all too amused.

“Why must you always do this?” Mr. Dugray laments, exasperated. “Why do you try to make living with you as intolerable as possible? Is it your goal to kill me?”

“No, that’d just be an added perk.”

Jess flinches when his stepfather slams his glass down on the table. “I don’t think you realize, Jess - you’re very lucky.”

“Careful, you’ll scratch the table,” Jess mutters. He scratches at the back of his neck, feeling suffocated by his collar and tie.

“I didn’t have to keep you when your mother died, Jess. I had no responsibility to, but I decided to let you stay with us.”

“What, just out of the kindness of your heart?” Jess sneers. “Maybe you should’ve kicked me out - could’ve saved us both a lot of trouble.”   
“I let you stay with us,” his stepfather continues forcefully, “and what did you give us in return? You’re rude, you refuse to follow any instructions, and you waste your Chilton tuition by failing all your classes...you have no future, Jess, no potential. You’re going to end up just like your mother if you continue behaving the way you do now.”

“You’ve been awfully quiet,” Jess says, turning to Tristan. “Got anything to add, huh? Got any winning insults to throw at me? I know you’ve been dying to share your material.”

“Do not add to this insanity,” Mr. Dugray instructs Tristan sternly.

“Why not? He doesn’t behave much better than me. Let’s get everyone involved and get this thing really started, huh?”

“Shut up, Jess,” Tristan sneers. 

“Oh, that one’s a winner!” Jess scoffs. “Smart. Really, really clever comeback. You know, if you just tried a little harder-”

“No one wanted you here in the first place. So why don’t you just-”

“Enough!” Mr. Dugray shouts, glaring at Tristan and Jess both. “That is _enough.”_ He presses a hand to his temple in exasperation. “How Tristan behaves is irrelevant - I am talking about you, Jess, and how _you_ continue to make everyone’s lives harder by simply existing.”

Jess clenches his jaw. It shouldn’t hurt - it shouldn’t hurt, but it does. 

“You don’t care about anyone but yourself. You torment me and your step brother both - your mother’s probably lucky she’s done with you so soon.”

Deep breaths. Deep breaths. Don’t make it worse than it has to be. He’s sat through this before, and he can again. 

“Who was that last girl you brought over? Tori?” Mr. Dugray laughs, but there’s no mirth to it. “How’d that go? Is she done with you yet?”

Jess grips his fork so hard, he’s sure there’s an indentation in his hand. 

“You mean nothing to anyone, and you make sure of it. This is all on you, Jess - whoever you end up being, no one here can take any credit for how much of a screw-up you’ll become. Not to mention-”

“Stop!” Jess shouts, the word escaping his lips before he can hold himself back. He stands up. “Just stop! What do you get out of this, huh? What kind of sad and empty little life do you have to lead to get off on haranguing your stepson? You said you didn’t want me here - so get rid of me. Throw me out. Cut me out of your life and pretend I never existed like you so clearly want to. Do it. Because I don’t want to be around either of you two any longer.”

Jess waits with bated breath and his stepfather slowly rises from his chair. “Get out,” his stepfather spits. “Get. Out.”

Jess glances over and sees Tristan’s stunned expression, and then looks back at his stepfather. Slowly, but surely, Jess takes off his tie and slams it down on the table. 

“Gladly.”

Without another world, he storms past his stepfather and up the stairs.

**

Jess drops his duffel by his feet and sits down on the curb outside the gates separating him from his now ex-residence. He fishes his cell phone from his coat pocket and dials the number he was given only a few weeks prior -  _ call if you need anything; a place to stay, a book to read, anything -  _ and waits. 

_ “Hello?” _

Jess closes his eyes and grimaces. He hates asking for help, showing any sign of weakness at all - just like when Rory was standing in front of him, he can’t find his voice.

_ “Hello? Who is this?” _

He takes a breath. “It’s...it’s Jess. Do you...can I take you up on your offer?” He cringes at the desperation in his voice.

Once he’s got the address, Jess thanks him and hangs up before dialing the number for the cab company. 

**

Jess thanks the cab driver and closes the door, shouldering his duffel bag. He crosses the street and descends the stairs to the apartment before knocking on the door.

A few moments later, the door opens, and Mr. Medina is standing there, a gentle look on his face. “You make it here okay?” He asks.

Jess nods.

Mr. Medina smiles sympathetically. He lets Jess in and closes the door. Jess shifts awkwardly, unsure of what to do or say.   
“It’s not much,” Mr. Medina says sheepishly, scratching the back of his neck.

Jess shakes his head. “It’s…” He swallows, trying to find his voice. “It’s nice. Really.”

Mr. Medina smiles. “Well, there’s the kitchen,” he says, gesturing, “the living area, and the bathrooms are over there.”

Jess looks around, taking a step further into the apartment. His breath catches in his throat at the large shelves of books against one of the walls. 

Mr. Medina smiles. “It’s quite a collection, although I’m definitely lacking some. You can look through it and let me know what I’m missing.”

Jess stares at his feet for a moment and takes a deep breath. “Thank you. You know, for…” 

“Of course.” 

“Where can I…” Jess trails off, lifting his bag.

“Oh, right. By the couch is fine.”

Jess drops his duffel by the couch, still feeling incredibly uncomfortable. “So…”

Mr. Medina hesitates before he speaks. “I understand if you don’t want to talk about this, but…” He sighs. “What happened?”

Jess clenches his jaw and avoids looking Mr. Medina in the eye. “It just...got to be too much.”

Mr. Medina nods and thankfully doesn’t press for more answers. “I told you a couple weeks ago that my door - my apartment door, more specifically - was open if you needed an out. I’m glad you took me up on it.” He pauses. “You can sit down, you know,” he says with a laugh. “I didn’t pay half my monthly salary for that couch just so people can stand next to it.”

Jess takes a seat and exhales slowly. Mr. Medina’s apartment is already more of a home than his stepfather’s house ever was, but he still feels incredibly out of place. (Although, is a home even a thing? He’s not quite sure if it exists.)

“I was going to order Chinese for dinner,” Mr. Medina says as he disappears behind a door and comes back out a few moments later with a pillow and some sheets. “Thoughts?”   
“Anything’s fine,” Jess replies. “I’m not too picky.”

Mr. Medina smiles. “There’s this place right by here that has the best lo mein - sound good?” 

Jess nods.

Mr. Medina grabs the phone while Jess reaches into his duffel and pulls out Rory’s copy of High Fidelity. He stares down at the cover, unable to bring himself to read.

“High Fidelity, huh?”

Jess flinches in surprise at Mr. Medina’s sudden nearness. “Yeah.”

“A new read, or have you read it before?”

“It’s a reread.”

Mr. Medina nods. “Figured as much. Everyone’s go-to Hornby, I’ve noticed.”

Jess’ jaw ticks as he continues to stare down at the cover. He feels a little guilty, having held onto it, but when would he have had time to give it back? And now Rory’s mad at him (and he’s mad, too, just in a different way), and he doesn’t know if she’ll ever talk to him long enough for him to give it back.

Besides, if he’s being honest, it feels good to still have a part of her with him. Even if they’re not on good terms, he still has something of hers, a reminder of what brought them together before it all fell apart. 

**

The takeout is pretty good, and as they eat, Jess finds that it gets easier to talk to Mr. Medina. It’s still a little awkward, staying over at his teacher’s apartment (part of him craves for the days when he thought his teachers lived at school - he catches a photo of Lorelai hidden under some books and wishes teachers didn’t  _ have  _ personal lives), but he thinks he might’ve found an adult he can trust, maybe for the first time.

**

“Jess?”

Jess glances up from the book he’s reading. “Yeah?”

Mr. Medina hesitates, uncertainty etched in his face. “You’ve been here about a week now, and I respect your privacy and all, but…”

Jess tenses. “What?” He asks, a little sharper than intended.

“I need to know...what happened with your stepfather? It’s my responsibility as your teacher - as an adult in your life - to make sure that you’re okay.”

Jess snorts. “You can opt out of this one - everyone else does.”

Mr. Medina sighs. “You know I’m not going to do that,” he says patiently, taking a seat on the couch next to Jess. “Now, I can sit here and wait as long as I need to, but I’m asking you Jess, as nice as I can, to tell me what happened.”   
Jess clasps his hands in his lap and stares down at his shoes, jaw clenched tight. It feels like an eternity before he finally finds his voice. “It’s not what you’re thinking. He just...he was yelling, like he always does, and I couldn’t take it anymore. And then he told me to leave.”

His teacher nods thoughtfully. “I know he’s been tough on you for a while,” he says after a moment to process Jess’ words. “That’s why I wanted to talk to you before the trip. You should have an adult in your corner, and I do what I can to be that person. You’re a good kid, Jess - don’t make that face, I’m serious - and you should not be forced to live somewhere where they don’t feel wanted. No one deserves that, especially a kid.”

Jess sniffs almost inaudibly, hoping his teacher doesn’t notice how much he is blinking.

“But...I think we both know you can’t stay here forever.”

_ There’s the catch.  _ Jess nods slowly, lips parted as he tries to find his words. “I know.”

“We don’t have to discuss this now. However, we will, at some point.” Pause. “In addition, the semester does start up again soon.”

Jess winces. “I don’t…” He closes his eyes and takes a breath. “I’m not ready. To go back,” he finishes lamely.

“Okay,” Mr. Medina says, accepting Jess’ response, much to his surprise. “I think the more pressing matter is finding someone to take you in permanently, and I don’t doubt that you can catch up on whatever you end up missing. But you have to go back at some point,” he adds.

Jess fidgets with his hands a bit. “I know.”

“There’s no rush to set any deadlines or anything, Jess. You’re not unwanted. I don’t want you to think that.” Mr. Medina smiles. “So. Pizza tonight?”

Jess lets out a shaky breath and nods. “Sounds good.”

“Alright.”

**

The rest of winter break comes and goes. Mr. Medina works on his lesson plan for the rest of the semester, while having Jess look over essays from his junior class and grade them. (Some of these papers - he wonders if half of these kids ever learned to  _ read.)  _ Jess works his way through Mr. Medina’s book collection and tries to keep to himself and not take up much space. 

Soon enough, it’s the end of break and school starts up again. Medina doesn’t press on him, and Jess doesn’t say anything about it.

A few days after break, though, there’s a knock on the door while Jess and Mr. Medina are eating leftover pizza. Medina excuses himself and goes to the door, and when he opens it, Jess catches a glimpse of curly black hair.

“What’re you doing here?” Mr. Medina asks.

“I don’t know,” a familiar voice admits. “I just...I wanted to see you.”

Mr. Medina sighs. “Lorelai…”

Jess freezes.  _ That’s  _ how he knows this woman - she’s Rory’s mom.

“Did we make a mistake, Max? Breaking it off?”

(Jess wishes he could disappear for a moment - he doesn’t want to hear this. He’s already intruded enough.)

_ “You  _ broke it off, Lorelai.”

“I know. But…” Lorelai hesitates. “Can I come in? Talking over the threshold is cool and all but - and why  _ do  _ they call it a threshold? I mean, is the thresh being held? What even is a thresh? I, uh, you’re an English teacher, so if anyone would know besides the creators of the Oxford English Dictionary…” She trails off.

Mr. Medina sighs again. “Not...not right now. I’ve got a - a friend crashing on the couch for a little while, and the place is a little cramped.”

“Oh. Okay. I...this was probably a mistake, anyway. I’m sorry.”

Mr. Medina waves his hand in dismissal. “Don’t worry about it.”

“Well...bye, Max.”

“Bye, Lorelai.”

The door closes, and Jess averts his gaze back to the half empty pizza box, pretending he didn’t hear a word. He’s sure Mr. Medina isn’t buying it, but he thinks his teacher appreciates the gesture all the same.

**

That night, Jess finds himself unable to sleep. Sure, he’s adjusted away from having to blast punk rock to drown out drunken fights in the living room of a decrepit New York apartment, that’s no longer an issue - but Lorelai’s visit sparked something, and now he can’t get out of his own head.

He knew going into this that he couldn’t stay with Mr. Medina forever, that this was only temporary, but he never thought of anywhere he could go next. But now - now, he might have to face the inevitable.

He staunchly refused to accept it as an option at first. That’s Rory’s town, her home, and stepping foot there could be considered invading enemy territory. And besides, he’s lived in cities his whole life - a small town doesn’t seem like something he’d like.

_ Where everybody knows your name,  _ he thinks to himself, remembering the conversation from what feels like ages ago.

Jess knows, though, that he doesn’t have another choice. He might not be happy about it, and it could prove to be a very bad decision, but when it comes down to it, he needs somewhere to live. Permanently. Asking his uncle to take him in, away from all the drama and torture of high-society Connecticut, is his best option. There’s nowhere else for him to go.

Maybe he was meant to end up in Stars Hollow all along.

**

“You sure your uncle will take you in?” 

Jess nods. “I called him. He said it’s fine.”

(He didn’t call, but Mr. Medina doesn’t need to know that.)

Medina nods. “Okay. But if you end up needing to stay here again…”

Jess attempts at a smile, but it doesn’t feel quite right. “I will.”

“Let me pay for the cab,” Mr. Medina offers, and Jess can’t do anything but accept.

As the cab drives away, Jess stares out the window, watching the brownstones pass by until they’re on I-84 on the way to Stars Hollow. It’s dark out, but Medina insisted on Jess helping him finish eating the pizza leftovers from the night before, and Jess wasn’t about to pass up a meal.

His heart rate skyrockets as they pass the  _ Welcome to Stars Hollow  _ sign.

Jess attempts to ignore his anxiety as he gets out of the cab and his eyes catch the  _ Luke’s  _ sign. The lights are partially on inside, and he can see Luke cleaning up.

Fighting the urge to run away, Jess takes a deep breath and knocks on the door. When Luke glances over and sees who it is, he walks over and opens the door hurriedly. 

“Jess?” His uncle asks, sounding bewildered.

Jess takes a breath, suddenly afraid to speak - it’s one thing to see his uncle now and then when he has to do damage control with Jess’ stepfather, but it’s an entirely different thing for Jess to seek him out and ask for his help.

“You got an extra couch for me to sleep on?” Jess asks, tensing and bracing himself for Luke’s answer.

Luke frowns in confusion, and Jess can practically hear the gears turning in his brain. “Sure.”

Jess lets out a sigh of relief. He steps inside the diner and Luke locks the door behind them. Wordlessly, Luke walks behind the counter and pushes past a curtain that leads to a flight of stairs. Jess follows him up the staircase and waits as Luke unlocks a door with faded letters on the glass.

The apartment is  _ tiny  _ and doesn’t look like it was ever meant to be lived in, but Jess is exhausted and wouldn’t care if it was the size of a shoebox as long as he had a place to sleep.

“Jess...what are you doing here?” Luke asks finally. “Is something going on? Everything okay at home?”   
Jess almost laughs at the word  _ home,  _ but he composes himself. “I got kicked out.”

“What? When?”

“About two weeks ago.”

Luke’s eyes widen in shock. “Two weeks ago? Where have you been living since - under a bridge? In the sewers?”

“I...I had temporary lodgings.”

“What’s all the vagueness for? Was it - was this a brothel or something?”

Jess snorts. “Hardly. My English teacher, Mr. Medina, he...he offered, so I accepted.”

“Okay.” Luke hesitates, brow furrowing in thought. “What happened with your stepfather?”

Jess exhales slowly. “Look, Luke, I’m really tired and I just need a place to sleep. Can we wait to talk about it?”

“Fine,” Luke concedes after a moment, “but we will talk about this in the morning, okay?”

Jess nods.

Once Luke has set up the couch for him, Jess falls asleep fairly quickly, but as he’s dozing off, he can’t help but think of who led him to this town in the first place. She’s close, now, maybe closer than he thinks. This thing he’s been doing, avoiding her at all costs - that has come to an end. He’ll have to face her sooner or later. 

For the first time in what feels like forever, Jess easily falls into a deep and dreamless sleep. 


	19. Rip it Up and Start Again

**Summary for the Chapter:**

> Rory grows suspicious when she sees a familiar face at Chilton. Luke establishes some ground rules for Jess.

Jess wakes up the next morning to a clanging noise and Luke swearing. Bleary-eyed, he sits up, rubbing his eyes. Luke is shoving items back into a closet and forcing the door closed, grumbling under his breath.

“Luke?” Jess asks wearily. “What’s going on? Are the Huns invading?”

Luke looks up, grimacing. “Did I wake you up?”

“It’s fine.” Jess sits up a bit, still adjusting to the bright lighting. “What, uh, what’re you doing? I think I’m a little too old for you to be childproofing the apartment.”

“No, no, I...I figured, well, since you’re going to be staying here for a little longer, I’d try to find something other than a couch for you to sleep on, but…”

“Instead you found the entirety of The Shaggs in there?” Jess asks, gesturing towards the closet. 

“What?”

“Nothing.” 

“Alright. Well…” Luke straightens up, eyeing the closet warily. “I’ve got a raft.”

“A raft.”

“Think of it as an inflatable mattress.”

Jess shrugs, holding back an amused smile for his uncle’s sake. “Whatever.”

Luke mutters something under his breath as he walks over to the fridge and opens it. “I’ll have to go to Doose’s to get anything edible,” he says, more to himself than to Jess. “What do teens eat? Trix? Is that still a thing?”

“Those are for kids,” Jess supplies, but the joke is lost on Luke.

His uncle shuts the fridge with a grunt. “Do you mind waiting to eat? I don’t have anything up here, and we haven’t started prepping in the diner yet.”

“Whatever,” Jess replies, remembering all too well the days back in New York when Liz didn’t bring any food home for weeks and he had to fend for himself. “I can wait.”

“Okay. Good.” Luke hesitates for a moment before pulling out a chair from the table so he can sit facing Jess. “I think we’ve put off this talk long enough.”

Jess sighs. He knew this was inevitable, and yet, the familiar urge to clam up at any particularly personal conversation is still present, and strong at that. 

“Why’d you leave, Jess? Why’d you come here? What, did you set fire to the house or something?”

Jess chooses to stare at and pick at a loose thread on his jeans rather than make eye contact with Luke. “No arson was involved in my escape.”

“Jess…”

Jess closes his eyes and takes a deep breath. “He told me to go.”

“Who? Your stepfather?”

Jess nods.

“He just...told you to go. No prompting or anything.”

Jess tenses. “We had a fight.”

“You’ve had those before.”

“Yeah, but this time I yelled back.”

Luke sighs. “Jess, the guy’s an ass, I know as well as anyone, but-”

“No, you don’t,” Jess says harshly. “You  _ don’t  _ know as well as anyone. You didn’t have to live with the guy or put up with his stupid business friends or endure his ragging on you constantly. Liz died, and you just-” Jess cuts himself off before he says anything he’ll regret.

Luke grimaces. He’s silent for a moment, absorbing Jess’ words slowly. “You’re right,” he admits, somewhat begrudgingly. “I know...I know things have been tough, lately, with your stepfather and...and Tristan, and all that, and I know we don’t know each other very well, but after your mother…” Luke pauses his rambling, trying to find his footing. “After your mother died, I know things got worse, but...”

“What are you trying to say?” Jess snaps.

Luke sighs. “I’m trying to say that I’m…”

“What, that you’re sorry?”

The look on Luke’s face lets him know that he got it in one.

Jess snorts. “Yeah, well…”

Luke opens his mouth and then closes it, and repeats the action, ultimately deciding to keep quiet and wait for Jess to speak. 

“I couldn’t stay there any longer,” Jess finally says, his voice nearly inaudible. “And I couldn’t think of anywhere else to go.”

Luke exhales slowly, his expression grim. “Okay. But if you’re going to live here...we need to set some ground rules.”

Jess looks up in surprise. “You’re letting me stay? Permanently?” He cringes at the undisguised hope in his voice that he didn’t bury quite in time.

Luke nods. “Yeah. I’m gonna let you stay.”

Jess feels himself relax just enough to breathe. “Okay.”

“But this has to be...we have to have rules,” Luke says, brow furrowed in concentration. “Figure out how this is going to work.”

“I figure you give me room and board. That’s as far as I got.”

“You’ll work in the diner. With pay,” Luke adds when he sees Jess open his mouth to object. “Not a lot of pay, but...pay. You’ll go to school and you’ll graduate. And…” He trails off at the look on Jess’ face. “This isn’t...this isn’t going to be like it was with the Dugrays. I’ll tell you that much.”

“I know. It’s just...Chilton.” Jess heaves out a sigh. “I can’t...I can’t go back there.”

“Why not? Did they kick you out or something?”

Jess shakes his head. 

“Then what was it?”

Jess’ jaw ticks. He doesn’t reply. 

Luke’s mouth sets in a line. “Tell you what,” he says after a moment. “Your tuition for the rest of the school year is paid, so you finish out sophomore year and we can reassess then. But you can take some time off - not a lot, but…time off.”

Jess bites his lip. “How much time?” 

“You can take next week off, but that’s it,” Luke decides. “No bargaining.”

Jess wants to argue, but he doubted Luke would even agree to take him in like this, with no notice at all - as little as he knows his uncle, he can tell he isn’t a fan of spontaneity - and he doesn’t want to risk it. “Okay.”

“That’s a deal?”

Jess almost smiles. “That’s a deal.”

**

“It’s gonna suck for a while. But eventually, it’s all going to be okay,” is what Lorelai said after Rory told her about everything that happened with Jess. One day after, and Rory still remains doubtful.

The thing is, she told herself not to get her hopes up. She tried to convince herself that Jess won’t be there and everything wouldn’t magically be okay between them even if he was. Mr. Medina assured her that Jess was okay, but it’s been four days now, and Jess still isn’t there.

At the end of the day, Rory makes a beeline for her locker in a rush to get home (or, more accurately, just get out of Chilton). She opens it and curses when her AP U.S. history textbook falls out and hits the marble floor with a loud  _ smack! _

She bends over to pick it up. When she stands up, Rory finds herself face to face with who else but Tristan. 

“You know, you’re gonna give some very special girl a heart attack someday,” she reprimands him angrily, shoving her book back in her locker and exchanging it for her coat. 

Tristan leans up against the locker next to her, looking amused. “You know, it’s strange. We haven’t talked at all since the ski trip,” he drawls.

“Oh, please, you are _ not  _ that daft.”

“What?” He asks innocently.

Rory slams her locker door shut and looks at him crossly. “You  _ know  _ what happened at the ski lodge. Why would I want to talk to you?”

“Hold up, I’m confused. Did I do something to you?”

“Yes!” She exclaims, turning pink when a couple of people look over. “Yes, you did,” she continues, a little quieter, but just as mad. “You shouldn’t have told me  _ that  _ when I was obviously upset and act like you’re doing me a favor. And you shouldn’t have said anything when it’s something that I should have heard from...not you.”

Tristan’s eyes grow wider. “You wound me, Mary. I was under the impression that we were friends.”

“Get out of my way.”

Instead, Tristan leans in more, backing her up and caging her against the lockers. “Look, I know we’re dancing around the topic, but don’t you think it’s better for our relationship if we just talk about it?”

“Talk about what?” Rory asks tiredly, giving up trying to get past him. 

“Jess,” Tristan says, as if it should be obvious.

(And it is, it is obvious, but Rory was  _ really _ hoping that just this once, she would get it wrong.)

“What about Jess? You already told me he’s your step brother, so you’re going to have to try a lot harder than that to-”

“Step brother?” Tristan repeats, cutting her off. “See, that’s the thing. We didn’t get a chance to catch up - a lot happened over break.”

“What do you mean?” Rory demands, her heartbeat picking up with worry. 

Tristan smirks. “I see I get to tell you the good news. Jess and I...we aren’t step brothers anymore. He left.”

“Where did he go?” She asks anxiously.

Tristan shrugs. “Dunno. Don’t care, really, as long as he’s gone.”

Rory opens her mouth to retort, but her breath catches in her throat when she catches sight of someone walking in the opposite direction of the headmaster’s office. 

Luke.

She blinks a few times in absolute and utter bewilderment, about to call out to him, but she stops herself.

What could Luke possibly be doing at  _ Chilton? _

And then a thought hits her, rendering her so stunned she could be knocked over with a feather. It’s a theory - not even a theory, just a  _ guess,  _ but oh my god, what if-

“Mary? Are you okay?” Tristan prods. “You look like you’ve seen a ghost or something.”

“Excuse me,” Rory mutters, ducking under his arm and hurrying away from him, just in time to see Luke get into his truck. 

She holds her books tightly to her chest and watches him drive away. She might as well have seen a ghost, that would probably have been less confusing (she’s lost count of how many times Lorelai has insisted Chilton _has_ to be haunted); however, this gets her thinking.

It’s not that she feels stupid for not having thought of it sooner, she’s not even sure she’s  _ right  _ (besides, if Luke hadn’t passed by just as Tristan was talking, Rory knows she probably wouldn’t have even considered this a possibility), but she isn’t satisfied, not in the slightest.

She feels similarly to when she was first getting to know Jess - that urge, that  _ itch  _ to know more and learn more and figure out every little thing about him. She’s getting that same itch now. 

She holds onto these thoughts the entire bus ride home, intent on finding out more as soon as she can, knowing she’ll have to put it on the back burner soon, at least for a little while longer. At least until after Friday night dinner.

**

“I cannot believe my mother,” Lorelai laments, shaking her head. “I mean, that bedroom - that was  _ insane,  _ right? That wasn’t just me?”

Rory laughs behind her mug of coffee. “It was so  _ pink,”  _ she chortles. “I mean, it was like walking inside a bottle of Pepto-Bismol.”   
“That’s exactly it! Thank you,” Lorelai exclaims, satisfied.

Rory swallows and sets her mug of coffee down on the table, glancing over at the curtain behind the counter. Throughout their dinner, Luke had been ducking behind it and going upstairs repeatedly, and at one point while Luke was pouring her mom more coffee, she’d heard a loud  _ thud  _ coming from upstairs. Either someone is up there, or Luke has some really active gremlins.

“What should we do for dessert?” Lorelai asks excitedly, grabbing the menu and flipping through it.

Rory gives her a look. “Didn’t we already decide on pie?”

“I know, but I’m in the mood for something different.”

“You’re so flighty. This is why you can’t land a man.”

“Keep this up and I’m telling Emily just how big of a Backstreet Boys fan you are,” Lorelai threatens.

Rory opens her mouth to reply, but then she remembers a discussion she had with Jess a few months ago where she somehow backed herself into a corner defending the underrated lyricism of boy bands from the nineties, so she keeps quiet.

“Hey, what’s up?” Lorelai asks, nudging Rory’s arm. “Was it something I said? I could change it to Nickelback if you want,” she offers with a smile.

Rory shakes her head and forces a smile. “I’m fine. I was just thinking about dessert. What if we tried the-”

“The Luke’s Diner dessert combination challenge of ‘95?” Lorelai asks, eyes wide. Rory grins. “Didn’t Luke threaten to kick us out forever if we tried that again?”

“What if we order each part separately? Maybe then he won’t walk away when we try to order it this time.”

“And then we can put it together at home!” Lorelai exclaims excitedly. “Good thinking. I knew you got into that smarty-pants school for a reason.”

“I can hear you plotting,” Luke reminds them from behind the counter, “and I will  _ not _ be indulging this behavior.”

“You’re depriving us of joy, you know.”

“I think I can live with that.”

Rory listens to them bicker for a while before she realizes something. She stands up abruptly, starting her mother and Luke. “Luke?” Rory blurts before having a chance to second guess herself. 

He looks over at her. “Yeah?”

“Can I get something from upstairs?” She asks hurriedly. “I think I left something up there. I left a...a book. Upstairs. When I went up there. A few months ago.”

Luke frowns. “Sure,” he answers confusedly. “But Rory, wait, there’s-”

She doesn’t catch the end of his sentence, already past the curtain and flying up the stairs. She stops at the door, hand raised to knock, but then she freezes. If this door opens and her theory is right - she hasn’t even thought about what she would do.

In the end, she knocks on the door.

“In a second,” a familiar voice calls from the other side of the door. Rory holds her breath in anticipation as she hears footsteps and then the door opens and then there he is, standing right in front of her for the first time in weeks.

Jess’ eyes widen. “Rory?” 

“Jess?”

It takes him a second to recover from the shock. “Aren’t we all dressed up?” He mutters, noticing her Friday night dinner attire. 

“What are you doing here?” She finally asks, laughing under her breath in surprise.

Jess stays silent for a moment, blinking and staring and suddenly, she feels sick to her stomach with the memory of what happened just a couple weeks prior. “I’m staying with Luke,” he says finally.

Rory bites her lip, struggling to think of what to say next. “But - why?”

It feels like an eternity before he answers. “I’m his nephew,” he says quietly, “and I needed a place to stay.”

They stand there in silence before Jess speaks again. “Rory, I-”

“No,” she says sharply. “There’s nothing you can say, Jess. There’s nothing you can say to...to make this right again. So just...drop it.”

Jess exhales slowly, his expression pained. When it becomes clear that he’s done speaking, Rory turns around and descends the stairs. She realizes only now how bad her legs are shaking. 

(She glances behind her before pushing past the curtain, hoping, but she hears the door click shut instead.)

She’s quiet the whole way home. 

**

“So Jess is Luke’s nephew?”

Rory nods. “Yep.”

Lane stares at Rory in shock, jaw dropped. “God, that’s so weird. Who would’ve thought that all this time…” She trails off, shaking her head in astonishment. 

“That’s the thing,” Rory replies, ducking under a particularly large piece of furniture that’s labeled as half-off. “Just the fact that they’ve been related this whole time…” 

Lane nods in understanding. “There’s a lot to unpack there.”

Rory bites her lip. “I don’t even know where to start.”

“Well-”

“Lane.”

The two girls stop walking up the staircase and turn around, facing a stern-faced Mrs. Kim. 

“Yes, mama?” 

“Where are you two going?”

“Upstairs, mama,” Lane replies. “Rory and I were just-”

“You finish your homework?”

“Yes.”

Mrs. Kim eyes Rory warily. “Alright. Dinner is at six.”

“Rory will be gone by then, I promise.”

Rory waits until Mrs. Kim is out of sight before she groans. “I can’t believe she still doesn’t like me.”

“Join a convent and maybe she’ll come around,” Lane offers.

Lane closes her bedroom door behind them before turning back to Rory eagerly. “Okay, back to Jess.”

“What about him?” Rory asks sullenly, taking a seat next to Lane on the floor. 

“I don’t know! What does him and Luke being related mean for you guys?”

Rory frowns. “I don’t even know. I’ve been so shocked that I haven’t even considered all that. I mean, I guess that explains Luke coming back from Hartford to deal with his nephew on the same day that Jess wasn’t at school, but…” And then something hits her, something so horrible that it makes her blood go cold and she can’t believe she hadn’t realized it until now.

“Rory? What just happened?” Lane snaps in front of her friend’s face. “Are you still with us?”

Rory winces. “If...if Jess is Luke’s sister’s son, and Luke’s sister is…if Jess is Luke’s nephew, that means Jess’ mom is...is dead.” She wraps her arms around herself. “And I...I said something about going home to his mansion and his mom when we fought and I didn’t even  _ consider _ the fact that his mom might be dead. With everything I knew, I just assumed she was in rehab or something.”

Lane looks at her friend sympathetically. “There’s no way you could’ve known.”

“I know. I just…” She bites her lip. “He was going through something terrible this whole time and he couldn’t even tell me. If I had known…” She sighs. “If I had known, I never would’ve said that to him.”

“What’re you gonna do?”

“I don’t know. I’m still mad at him, but I still…” She trails off.

Lane frowns. “You still what?”

Rory shakes her head. “Never mind. It doesn’t matter. Whatever I felt, it doesn’t matter anymore. I told him it was over and he couldn’t make it right, and I meant it. I meant it, but...”

Lane hesitates for a moment. “Well, it probably hurt when he didn’t chase after you and didn’t fight to stay friends with you even when you told him all that. Especially if you’d both been so important to each other.”

Rory swallows. “Yeah.”

“Maybe you misread some things, but that doesn’t make you a bad person.”

“I guess,” Rory mumbles. “But why did he have to come here? Did he really not have anywhere else to go? I was getting past this,  _ him,  _ and now that he’s here…”

“Whatever happens,” Lane insists, “I’ve got your back. Okay?”

Rory looks over at Lane and smiles softly. “They just don’t make friends like you anymore, do they?”

Lane grins. “Well, I  _ am  _ one of a kind…”

“Never change,” Rory mumbles, resting her head on her friend’s shoulder. 

Lane wraps an arm around Rory and smiles. “I’ll do my very best.”

**

Lorelai excitedly plops down on the couch with a pack of Red Vines. “Dawson’s Creek night!” She exclaims excitedly, reaching for the remote.

Rory smiles. “Are you excited or something? I can’t tell.”

“Oh, boo, you’re just bitter,” Lorelai says, waving her hand in dismissal. 

“Hey, if Jen and her therapist have an affair it’ll be justified,” Rory warns right before the phone rings. “I got it,” she tells her mom, making her way over to the phone with a spring in her step.

“Much appreciated.”

Rory picks up the phone. “Hello?” 

_ “Hey, Rory.” _

Rory winces at the sound of Dean’s voice. “Hey, Dean,” she says as cheerfully as she can, but it sounds forced, even to herself. “How’s it going tonight?”

_ “Pretty good. You?” _

“I’m good,” Rory tells him, although suddenly she feels anything but.

_ “I’m glad. I was wondering, though, if you wanted to hang out tonight? Either at your house or mine, it doesn’t matter, but I wanna see you.” _

Rory glances over at her mom. “Dean, I don’t know...I told you, I watch Dawson’s Creek with my mom on Wednesdays…”

_ “C’mon. You can miss one, right? It won’t kill you or anything.” _

“I already missed one because you wanted to hang out.”

_ “That was months ago, Rory.” _

“I know...I just…” She can feel herself starting to cave. “I…”

“Hey, Rory?” Lorelai interrupts. “Can you tell him to wait just one second?”

Rory nods. “Dean, just one second, okay?” She doesn’t wait for a response and covers the receiver so he won’t hear. She looks at Lorelai expectantly.

Her mom sighs, her expression grim. “Honey. I want you to tell him that you can’t hang out tonight because you have plans. Okay?”

“But-”

“Rory.”

Rory looks down at the phone anxiously before bringing it back up to her ear. “Sorry about that, Dean. My mom had a question about something.”

_ “So, what do you say?” _

She squeezes her eyes shut and takes a breath. “...Not tonight, Dean. I...I’m sorry, but I have plans and they’re kinda important to me, so...I’m sorry. I can’t.”

Dean is silent for a moment.  _ “FIne.” _

“You’re mad,” Rory worries, distressed.

_ “I’m not mad. Why would I be mad? A stupid TV show is more important to you than your boyfriend. Whatever.” _

“A show that I watch with my mom.”

_ “It’s fine, okay? I mean, I doubt you’d say no to  _ Jess,  _ or whatever, but it’s fine.” _

“Dean, it’s not like that, I-”

_ “I have to go.”  _ The other line clicks and she knows he’s hung up.

Rory slowly puts the phone back and sits down on the couch, not looking over at her mom, who keeps glancing over at her as they watch. The episode is good, she doesn’t  _ not  _ like it, but the entire time, Dean’s phone call just doesn’t sit right with her.

Maybe she can make it up to him tomorrow.

(But she keeps thinking - should she even have to?)

**

It’s a long week, and by Friday, Rory is exhausted. She’s managed to avoid seeing Jess, even if it means refusing to eat at Luke’s and taking the long way around to get to the bus stop. He hasn’t been at school, but she doesn’t allow herself to wonder why. It’s been a week, and he hasn’t tried to see her either or explain himself, so she figures the feeling is mutual. 

After Friday night dinner, Rory tells Lorelai she’ll meet her at home and heads to the bookstore. She’s getting that itch again, and besides, she still hasn’t gotten her copy of High Fidelity back, so it can’t hurt to replace it. 

She walks through the aisles, looking around and browsing. After a few minutes, though, she turns the corner and finds Jess. She wants to turn back and run out, but as she stares at him, she starts to soften, remembering all the things she’s realized.

Jess looks up from the book he was looking at, his expression turning stony when he sees her. She stiffens, her sympathy disappearing at the look on his face. “What’re you doing here?” Rory asks, crossing her arms over her chest, 

He gives her a look. “I’m casing the place. What does it look like I’m doing?”

She glares at him. “You don’t need to be rude.”

“You march in here and act like I’m doing something wrong by being in a bookstore,” he fires back, “in the town that I live in. What do you want from me, Rory?”

“I don’t want anything except for you to leave me alone.”

He scoffs. “Jeez.”

“Things were going just fine when we weren’t speaking.”

“Yeah? And which part of the last few weeks was that? This past week where you’ve been avoiding me at all costs? Is it when I was stuck at my stepfather’s house over break and had to deal with him and  _ Tristan  _ every day? Or was it when you told me you wanted me, totally unprompted, and then cut me out of your life for what appears to be for good? Can you tell me? ‘Cause I just can’t figure it out.”

“God! I can’t believe you!” Rory exclaims. “You couldn’t have gone anywhere else? You just had to move to the town where I live? Just to torture me?”

“Trust me, I’m not thrilled about the arrangement either,” he sneers. 

“So then why don’t you leave?”

“You must’ve realized it by now,” Jess retorts. “I know you’re not stupid. You know what the deal is my mother, and my stepfamily isn’t exactly the Bradys. Unless you’ve got any other suggestions, you’re going to have to learn to deal with it.”

Rory huffs. “I don’t.”

“Didn’t think so.”

“You know, I’m actually glad that we ran into each other.”

“Oh, yeah?”

“Yeah. ‘Cause there’s something I’ve been needing to tell you, and this seems like the perfect time, doesn’t it?”

He raises an eyebrow. “Well? Don’t leave me hanging.”

She raises her chin. “I know that at the ski lodge, I told you I liked you, but...that was a mistake. Things had just been weird with Dean lately, and I was just...confused. I didn’t mean it. I don’t...have feelings for you.”

Jess is silent for a moment. “Good,” he finally says. “Wouldn’t want to keep you disappointed.”

“Good.”

“So, it’s settled.”

She looks away from him. “Yes, it is.”

“Fine.”

“Fine!”

“You know, you can hate me all you want,” Jess snaps, “but I don’t think you’re angry at me. I think you’re angry at yourself, but you refuse to accept it, so you take it all out on me, like you’re some elementary school bully on an after school special.”

“And what makes you think that?”

“You’re the one that ruined things and you know it,” he all but yells. “So parade around on your high horse all you want, but deep down you know that I’m not any more at fault than you are.”

Rory glares at him. “Why were we ever friends? It’s not like we can stand each other at all.”

“Beats me.”

“‘Cause there’s nothing here,” she continues angrily. “Like I said. It’s done.”

“Then you might want this back.” J ess reaches into his back pocket and pulls out her copy of High Fidelity. “Take it,” he says, holding it out. “You can save some money. Besides, I don’t really want to see it around.”

Rory stares at it for a second before snatching it out of his hand. Without another word, she storms away for what feels like the hundredth time, leaving Jess behind. 

**

That night, after completing her homework for the night, Rory closes her laptop and looks around her room. Her copy of High Fidelity seems to be mocking her as it sits on her desk, so she grabs a box from the front hall closet and tosses the book in.

For good measure, she takes her copy of  _ The Tell-Tale Heart  _ from her nightstand and adds it to the box. Soon, everything she could think of that reminds her of Jess is sitting in it. 

She shoves the box back into the closet and shuts the door.

But even then, he doesn’t leave her mind. She can get rid of anything that reminds her of him, but she can’t remove him from her life. 

Rory can tell him she doesn’t care all she wants, that she’s done with him, but the reality is, she knows it’s not true. Being at odds with him is killing her, but she can’t see through his guard long enough to tell if it’s killing him, too. 

And if he showed up at her door, saying he wanted her, too - she knows she would forgive him.

For better or for worse, this heartbreak isn’t going to heal anytime soon. No matter how much she wants it to. 

**

After leaving the bookstore, there’s a heaviness in Jess’ chest that won’t go away. Even as he climbs the stairs and walks into the apartment above the diner, he feels weighed down. So he takes a seat, grabs a pen, pulls out the notebook he bought at the bookstore, and begins to write.

And write, and write, and write. 


	20. Vanity Fair

**Summary for the Chapter:**

> Jess makes a new acquaintance, which ends up upsetting Rory.

**Notes for the Chapter:**

> IMPORTANT: please take the time to copy/paste the link below and check it out. Sign petitions and donate if you can. 
> 
> https://blacklivesmatters.carrd.co/

Jess steps into the bathroom, tie in hand. He stares in the mirror as he crosses one end over the other and follows the familiar steps. He leaves it a little loose, just because he can. 

He checks his hair before closing the bathroom door behind him, the door clicking shut. After lacing up his shoes, Jess grabs his messenger bag off the table and his coat off the chair and walks out of the apartment.

(Over the past week, Jess took care to memorize every nook and cranny of the diner. He doesn’t love it - the apartment is way too small and the patrons are just way too weird - but Jess is always going to be at least a little bit grateful to this place.)

Pushing past the curtain, Jess takes a muffin from the display, ignoring his uncle’s objections. 

“Take the truck,” Luke calls after Jess, tossing his nephew the keys. Jess nods in thanks and exits the diner, the bell chiming in a way that is already familiar. 

The drive to Chilton isn’t very long, but Jess still has time to think. He knows that this is probably for the best, even if he doesn’t like it. But he also knows he’ll have to see Rory, and that fills him with a sense of dread that makes him want to cry based on the sheer fact that the feeling exists. 

It’s not that his feelings for her are gone. It’s that they’re still there, but hers are not - yes, she could be lying, but what reason does he have to not believe her and not take her at her word?

Regardless, he still feels like a bit of an idiot.

**

After second period, Jess stops by his locker to grab his notebook for his next class that he definitely will not end up touching. It was somewhat of a comfort to see Mr. Medina before anyone else; there’s a level of  _ trust  _ there now that Jess has never had with any adult previously. He thinks he likes it, though, barring the foreboding feeling that eventually, it’ll be broken. 

“Jess.”

Jess nearly jumps out of his skin, closing his locker door. “Jeez, you nearly gave me a heart attack.” He turns his head to see who he’s talking to. A girl he doesn’t really recognize is standing at his side, holding a couple textbooks. 

“You’ll probably survive,” she ventures with a shrug.

Jess shakes his head amusedly and leans up against his locker. “Do I know you?” He asks, unbothered.

“Do you know anyone here?”

“Good point.”

“I’m Zoey,” she answers. “We have Econ together, but I doubt you’d recognize me. I sit in the back - you know, by that blonde kid. The asshole. What’s his name? Triton or something?”

“He wishes,” Jess quips. “You have my attention. You need me for something?”

“That depends,” Zoey says mysteriously. “What’s going on with you and...I think her name is Rory?”

Jess inhales sharply and winces. “Uh...yeah, that’s her name. And what do you mean?”

“Well, even though I wasn’t on the trip, I think  _ everyone  _ has been informed of your little screaming match outside the bus-”

“Great,” Jess mutters.

“-but I was just making sure that there’s nothing...going on between you two.”

Jess swallows. “No, there isn’t.” It feels oddly final, saying it out loud.

“No, you don't have any feelings for her, or no, you’re not dating but you’re still super into her?” She snorts at the look on his face. “Please. Anyone with half a brain can tell that you’re basically head over heels for her.”

“I’m not-“ He huffs. “Can everyone tell?” He asks tentatively as an afterthought. 

Zoey smiles sympathetically. “I wouldn’t worry. Not many people here have half a brain.”

“Yeah, well...she doesn’t have feelings for me, so.”

Zoey frowns sympathetically. “I’m sorry.”

Jess shrugs for a lack of anything better to do. “Why do you ask?”

“Well, that comes down to why I approached you today,” she says. “I have an offer.”

He raises an eyebrow. “An offer.”

“Yes.” Zoey tucks her curly blonde hair behind her ear and straightens up in an attempt to seem professional. “Look. You’ve got feelings for Rory and you need a distraction, right? So, I’m offering one.”

“A distraction.”

“Is this going to turn into a ‘repeat everything I say’ gimmick?” 

He opens his mouth slowly as if intending to repeat her before laughing under his breath. “I’ll spare you. So, you have an offer?”

“Okay, so, when I came up with this, it  _ seemed _ like a good idea, but now I’m doing that second guessing thing that I always do before asking people for something.”

He smiles.

“You need a distraction. And I find you attractive, you know, to a certain point-“

“Gee, thanks.”

“-so, I was thinking. You and me, totally casual, friends with benefits type thing except not friends with benefits because I hate that phrase and it always leads to some big problem in all those teen dramas - except for that weird thing with Pacey and Jen, but anyway - but that’s the idea.” She frowns when he stays silent. “Oh, god, you think I’m some type of whore, don’t you?”

“No, no,” he assures her quickly with a laugh. “I don’t. I just…you…” He glances behind him in the direction of Rory’s locker and Zoey follows his gaze. 

“Caught you off guard?” She offers, her tone soft as if she’s implying something. 

He nods. “Yeah.”

She smiles. “Thought so. This is totally optional, and if it weirds you out, by all means, say no. But you seem like you could use a little bit of a…”

“Distraction,” Jess offers. 

“Exactly,” Zoey confirms. “You need to forget for a bit, I’m guessing.”

He shrugs, but he’s sure she can tell the answer is yes.

“It’s a totally ‘no strings attached, can turn each other down at any point if we’re not in the mood’ situation.”

Jess finds himself nodding slowly at first but then a little more assured. “Okay.”

“I do have a few terms to agree on, though.”

“Did you bring a contract or something?”

“No. But I thought about it.”

“Fair enough.” Pause. “And your terms are…?”

“Oh, right.” She lifts her chin up a bit, as if that will make her a little bit taller than her height of approximately 5’4”, if Jess were to guess. “This isn’t to make anyone jealous, for either of us. That’s a kind of 90210 or Ross and Rachel thing that I really don’t like, so that’s a no go.”

“Understandable.”

“Second...actually, I didn’t think of a second one,” Zoey admits. “Too many rules kind of defeats the purpose, anyway, right?”

“You’re not gonna tell me not to fall in love with you or anything?”

“It’s inevitable,” Zoey jokes, and Jess laughs. 

“It’s a deal.”

“Good.”

Zoey stands still for a moment. Then, before he knows it, she’s kissing him.

**

A couple days later, and somehow, Rory and Jess have managed to avoid a single interaction. Sure, it takes a little maneuvering, but neither is very willing to face the other for whatever reason. 

(Reasons that they are both painfully aware of.)

It’s Jess’ first Thursday back at Chilton when their pattern breaks.

Seeing Jess continues to be a knife to the chest, whenever it happens, but Rory has managed to avoid any run-ins so far. 

So, of course, she has to collide with him while walking down the hallway towards her next class, dropping all her things and watching them scatter around the floor.

Rory forgoes the apology and begins to pick up her things as fast as she can, her face on fire. She reaches for her notebook, but another hand picks it up first. Looking up, Rory sees a blonde girl with curly hair offering her her notebook.

“Thanks,” Rory mumbles as she stands up and takes the notebook, still embarrassed.

“No problem,” the girl says with a smile. Rory glances over at Jess involuntarily - it’s almost a reflex, one she has yet to unlearn - but he isn’t looking at her.

He’s looking at the girl. 

That’s when another pain hits, a different kind, so subtle she might’ve missed it if she hadn’t been paying such close attention to Jess. 

Rory swallows, torn between her reflex to apologize, her desire to storm away in a huff, or her curiosity - and her journalist tendencies win over.

“You got everything?” The girl asks.

Rory nods stiffly. “Yeah.”

“Good. Last time I tripped, I dropped my note cards all over the hallway. Getting them back in order was a nightmare.”

Rory forces a weak smile.

The girl turns back to Jess, her curls bouncing. “I’ll see you in my car after school?” 

Jess nods. 

The girl smiles and kisses him before waving good-bye to Rory and walking off towards her next class.

Rory watches her go, her stomach bottoming out, due to shock or what, she’s not sure. She turns her attention back to Jess, that same pain in her chest. 

“Her name is Zoey,” Jess answers her unasked question.

Rory nods awkwardly. She can feel an anger building, growing stronger as she looks at him. He’s so casual, so nonchalant, when what just happened was earth shattering. “You move on quickly,” she blurts out.

Jess’ expression remains unchanged. “Move on from what? You made it quite clear there was nothing between us, remember?”

“So, what is she? Your girlfriend?” Rory demands.

“What’s it to you?”

She grips her books tight. “Nothing. Just thought I’d ask.”

“It’s casual,” Jess says calmly. 

“Casual,” Rory repeats. 

“You have a problem with it or something?”

“No,” Rory snaps automatically. “I couldn’t care less, really.”

“Okay.”

“You’ve just...never mentioned her before, that’s all.”

“Well, I only met her a couple days ago.”

“Didn’t take you very long to get cozy, did it?”

Jess scoffs. “You’re being ridiculous. I’m leaving.”

“Thanks for the heads-up.”

They both storm off in opposite directions. Ducking into the bathroom, Rory still feels like they’re miles apart.

**

Rory takes a shuddering breath, trying to calm down. She wipes her eyes, but a couple more tears leak out. She squeezes her eyes shut, willing them away.

After a moment, she sniffs and exits the stall. Her eyes are already pink and puffy, so she turns on the sink and rinses her face. Another sob threatens to come out, but she holds it back.

The bathroom door opens, and in the mirror Rory can see a familiar face walk over to the sink beside her.

Zoey starts to wash her paint-covered hands. “Art project gone wrong,” she explains when she catches Rory staring. 

“Right.”

Zoey, seemingly unbothered by Rory’s stiff tone, gets more soap from the dispenser and scrubs a little harder. “You’re Rory, right?”

“That’s me.”

“Well, it’s nice to formally meet you,” Zoey says brightly. 

“Yeah, likewise.”

Zoey turns the faucet off and turns to Rory, her hands still dripping wet. “Is everything okay?”

“Just peachy.”

The blonde girl frowns, appearing confused by Rory’s continued coldness. “‘Cause, you know, if you wanted to talk - I know we don’t really know each other well, but isn’t that what bathrooms are for?”

“According to  _ Seventeen.” _

“So?” Zoey asks nervously.

Rory looks away. “I said I was fine. You want it in writing?”

“Did I do something?” Zoey asks, confused.

“No.”

“Oh. ‘Cause it seems like...but never mind,” Zoey says hastily. She goes back to scrubbing the paint off her hands in silence for a moment. “Because if I...somehow upset you, you could tell me, you know.”

“You sound like you already have a theory,” Rory grumbles, “even though you don’t know me at all.”

“Yeah, but I know Jess.”

Rory rips out a paper towel from the dispenser. “How? You’ve known him for three days.”

“Okay, maybe I don’t  _ know  _ know him, not yet, anyway, but-” She pauses to get more soap. “He’s...hard to read, but…”  _ Understatement of the year,  _ Rory thinks bitterly. “You seem important enough.”

“Trust me, I’m not,” Rory snaps. 

Zoey sighs. “Well...sorry. I shouldn’t push. I do this meddling thing, which is a really bad habit, but sometimes I just...slip right into it.”

“It’s fine,” Rory mutters. 

Zoey nods. She gets a paper towel, having finally scrubbed all the paint off her hands. “I’ll...see you around, I guess.”

“Sure.”

Rory only feels a little guilty when the bathroom door closes behind Zoey, but she quickly shakes it off. She wants to start crying again, but she’s spent too much time already hiding in a bathroom stall and crying over a boy that isn’t even hers. She’s reduced herself to a cliche, and she hates it.

And yet, she can’t shake off the image of Jess kissing Zoey for the rest of the day.

**

“Did you hear about the fundraiser?”

Rory looks up at Paris. “What?”

“The fundraiser. You know, an event held to raise money. Jeez, you’re slow in the mornings.”   
“I know what a fundraiser is. But I haven’t heard about this one, no.”

Paris doesn’t stop her brisk strides down the hallway, leaving Rory struggling to keep up. “They’re holding this fundraiser at the G. Fox ballroom - you know, the one with the criminally lax security - to raise money to plant a new tree in the quad.”

“I thought that was the senior gift.”

“They changed their minds. Again,” Paris adds with an eye roll. “I’m sure it’ll be back to a tree in no time.”

Rory frowns. “So, then they’ll cancel the fundraiser?”

“No, the fundraiser is happening,” Paris says, “not that we need  _ another  _ dance. I’m out of cousins to ask.”   
Rory stifles a laugh. “Well, it could be fun,” she offers, but she remembers what happened at the last Chilton dance she went to and her stomach turns a bit. 

Paris snorts as they stop at her locker. “Yeah, well. I’ll believe it when I see it.”

Paris continues to talk about the dangers of hosting the dance at a public property, but Rory zones it out. She looks over her shoulder, watching a blonde girl leaning up against her locker and talking to a girl that Rory doesn’t know. 

“Hey. Earth to Gilmore!”

Rory blinks in surprise and looks back at Paris. “What?”

Paris gives her an exasperated look. “I was  _ talking  _ to you.”

“Right. Sorry.” She tries to look attentive as Paris launches back into her lecture, but Rory’s gaze drifts back over to Zoey. “Paris?” 

Paris rolls her eyes at being interrupted. “What?”

“What do you know about that girl?”

Paris follows Rory’s line of sight. “Zoey Sinclair?”

“I guess, yeah.”

“Hm. Not much,” Paris replies after a moment of thought. “I mean, I’ve gone to school with her since first grade, but we were never close or anything. Average run-of-the-mill private school girl, I guess. Not super social or anything - but she’s not a recluse.”

“Oh.”

“Why do you ask?”

“Oh, no reason,” Rory says quickly. “So, are you going to that dance, then?”

“Does it have something to do with the fact that I saw her with Jess the other day?”

Rory blanches. “What makes you say that?”

Paris eyes Rory suspiciously. “You know they’re definitely sleeping together, right?”

Rory turns pink and stares at the floor. “It’s not about Jess.”

“Oh, it  _ definitely _ is,” Paris observes, a little too gleefully for Rory’s taste. "Are you  _ jealous?” _

Rory holds her books tighter and doesn’t reply. 

“What’s going on with you and Jess, anyway? You  _ still  _ haven’t told me the details.”

“I figured you’d heard the gossip,” Rory mutters.

“Yes, but it’s such a warped game of telephone that I can be pretty sure you didn’t - hey, where are you going?”

“Away from this conversation,” Rory says, walking quickly away, Paris tailing her.

“C’mon. Tell me!”

“No!”

Rory turns the corner and past the bulletin board, but something catches her eye. She slows to a stop. She vaguely remembers Mr. Medina telling the class about a journalism-centered trip to New York - she’d forgotten about it amidst all the drama - but here’s the flyer, right in front of her, and if she believes in signs, she knows this counts. 

“You walk surprisingly fast,” Paris grumbles, coming to a stop. “What’re you looking at?”

Rory shakes her head. “It’s nothing. But  _ stop  _ asking about Jess. I don’t want to talk about it, okay?”

“Okay, okay.” Paris rolls her eyes. “And people think  _ I’m  _ extreme.”

They walk to their next class, but Rory can’t help but think she might have found a way to escape - at least for a little while.

**

At first, Rory wasn’t even considering attending the dance. It just seemed unnecessary and a recipe for disaster - something she would prefer to avoid.

After catching Jess and Zoey walking off together, though, something in her snaps.

She goes to Doose’s after school. It’s not too difficult to find Dean - he’s restocking corn starch, funny enough, and she approaches him, feeling an odd sense of  déjà vu.

“Dean?”

He grins when he sees her. “This is a nice surprise.” 

She tries to smile. “Yeah, I thought I’d come see you after school.”

“Well, I’m not complaining.” He leans in and kisses her. “So, what’s up?”

“I actually had something to ask you,” Rory tells him nervously. “If that’s okay.”

“What is it?”

“Well, there’s this - the student government is hosting a fundraiser, a dance type thing...I wasn’t going to go, but, uh, it might be fun. It seems fun. And you’re my boyfriend, and you go with your boyfriend to these things, so I was hoping…” She trails off with a slight wince on her face.

Dean grimaces. “Depends. Is  _ Tristan  _ going to be there?”

“I don’t know,” Rory admits. “But please don’t let him ruin it. This is about you and me, not him, right?”

“And what about Jess?”

Rory decides to stare at the cabbage selection rather than Dean. “He won’t be there.”

“Okay.”

She looks at him in surprise. “Really?”

Dean nods. “Yeah. Could be fun, right?”

Rory finds herself smiling, more due to relief than anything. “You’re probably gonna have to wear a tie.”

“You’re making this so much harder to agree to.”

“You’re right. Sorry.” She takes a breath. “Thank you, Dean. It’s, uh, it’s two weeks from Saturday. Starts at eight.”

“I’ll pick you up at seven-thirty, then,” he says with a smile.

“Thank you so much. I owe you. Big time.”

He shrugs, but he looks quite satisfied. “I’m a saint.”

**

Asking Dean seemed like a good idea in the moment, it really did, but when Rory sees Jess in the hallway the next day, she suddenly remembers why she was putting space between her and Dean in the first place.

But she doesn’t have Jess to turn to now.

On Friday, at the end of first period, she approaches Mr. Medina. “Hey, Rory,” he says with a smile as he erases the chalkboard. “How are you doing?”

“I want to sign up for the trip,” she blurts out.

His expression brightens. “I’m glad. I think it’ll be good for you.”

“How do I…”

“Here, one second.” Mr Medina fishes threw one of his desk drawers before pulling out a form and handing it to her. “Give this to Lor - to your mother to fill out and hand it in to me by Monday.”

“I can do that,” Rory tells him with a smile.

“Good. We’ll be happy to have you there. And uh…” He smiles sheepishly. “You wouldn’t mind rooming with Paris, would you?”

**

The trip is over the weekend before the dance. As Rory sits on the bus next to a dozing Paris, watching the city fly by, she can’t swallow the feeling that while she’s working towards something, she’s also running away. 


	21. Manhattan Transfer

**Summary for the Chapter:**

> Rory visits New York on her class trip.

**Notes for the Chapter:**

> Apologies for the long wait, again - classes are over, but I'm still facing a little bit of writer's block, so. And also, apologies for the short/boring chapter. The next few are very packed and exciting, I promise!

Rory throws her suitcase down on the bed closest to the window. Paris insisted on taking the bed by the wall, citing studies on sun exposure and other things that Rory can hardly pay any attention to. The drive up was long, and all Rory wants to do is collapse onto her bed and sleep the rest of the day away. However, that unfortunately isn’t an option - she’s got about an hour to shower and change before they head to dinner at John’s Pizza of Times Square.

Paris sits down on her bed tentatively, rocking back and forth a couple times before patting the comforter firmly. “Just as firm as I like it,” she announces.

“Wonderful,” Rory mutters. “I’ll alert the Times. Or better yet, I’ll tell them in person tomorrow - this kind of breaking news, I feel like I should relay it in person, you know?”

Paris raises an eyebrow. “What’s with the attitude? I mean, don’t get me wrong, I’m digging it, but it’s so not…’fairy princess, bat my eyelashes, I’m so pretty’ of you.”

“I’m just tired.”

“The ride was only two hours and eighteen minutes. You can’t possibly be  _ that _ exhausted.”

“Did you time it?”

“Of course I did, but that’s besides the point. You’re grumpy, Gilmore, and all the sexist assholes out in the world will eat you alive if you don’t keep up with your sunny, look-at-me-I’m-a-Disney-princess disposition.”

“How very Sean Connery of you.”

Paris gives her a look. “What’s wrong with you?”

Rory begins to unpack her suitcase, shooting Paris a glare. “Nothing is  _ wrong  _ with me.”

“I didn’t even know you were going on the trip.”

“It was a...last minute decision,” Rory says curtly.

“Apparently. What made you change your mind?”

Rory slams a dresser drawer shut. “How were you not casted in LA Confidential?”   
“Rory.”

Rory lets out a long sigh and sits down on the bed. She traces shapes in the comforter instead of looking at Paris. “It’s a good opportunity. It would be really stupid of me to pass it up. I mean, the  _ Times?  _ That’s the dream,  _ my  _ dream - how could I not go?”

Paris frowns. “And?”

“And what?”

“What about Jess?”

Rory snorts. “I’m sure that girl is keeping him occupied enough. I doubt he’s even realized I’m gone.”

“That’s a load of bull and you know it. That guy is-”

“Don’t say it,” Rory snaps.

“What happened between you two?” Paris asks again. “Come  _ on,  _ Gilmore, you’ve waited long enough. You two went from  _ Butch Cassidy and the Sundance Kid  _ to the Greasers and the Socs in ten minutes, and I have yet to hear why.”

Rory picks at a loose thread on the comforter. “What have you heard?”

“Oh, the usual gossip. Nothing I could see you doing.”

Rory turns red. “Paris.”

“So?”

“Fine.” Rory looks up and takes a breath. “I told him I...I told him I liked him, and he didn’t say anything, and then we fought the next day, and - it was  _ horrible,  _ one of the worst fights of my life. And now…”

She swallows. “And now, we’re just…”

“Not getting along,” Paris suggests. 

Rory nods. “Yeah.”

“And do you still…?”

Rory shakes her head. 

“Why not?”

Rory hesitates. “I can’t,” she says finally. “I just...I can’t.”

“You’re better without him, I’m sure,” Paris supplies. “Behind every strong woman is a man who never bothered to learn emotional intimacy or how to tie his shoes.”

Rory doesn’t reply, instead deciding to stare intently at the carpeting. 

“Or, you know, he might pull his head out of his ass and see the light,” Paris adds, no doubt taking note of Rory’s less than enthused reaction. “You’re a catch, Gilmore. He’s gotta see that eventually. If he doesn’t, well…” She shrugs. “His loss. The idiot.”

Rory sniffs. “Yeah, well...were you planning on showering? ‘Cause I was just about to.” She asks, changing the subject. 

“Go ahead.”

Once she undresses and gets in the shower, adapting to the less than favorable water pressure a three star hotel will give you, Rory closes her eyes for a moment and takes a few steadying breaths. Thinking about Jess, it’s a painful thing, and all her memories are a load bearing wire, and the slightest tug will cause her to unravel. 

She wonders what Jess is doing right now - or, who he’s doing, she thinks bitterly - and immediately regrets it.

Why wouldn’t he move on? He’s a guy, and an available one, at that. She should’ve expected that he’d find someone sooner or later, why not, he’s a catch - it’s unfair of her to wish that he’d just mope around a little bit longer before turning around and making out with the nearest available girl. But then she thinks about Zoey’s hand on his chest and his hand in her hair and her comment about  _ meeting him in her car _ and she almost cries. Jealousy, it’s unbecoming, but it’s a feeling that’s becoming all too familiar.

Maybe she dodged a bullet. Maybe this would’ve happened sooner or later, and it’s good that it’s now because she can  _ move on.  _ She’s not sure she would’ve been able to do that if they were still friends. She doesn’t know how he feels about Zoey, if it’s love or like or just sex. Rory isn’t sure which one is worse. 

See, all she can do is keep moving, and the pain will slowly fade. She came to New York to get away from him.

And yet, all she is able to do is dwell.

**

“Jess, those customers over there-”

“I got it,” Jess grumbles, taking the coffee pot and a plate of eggs over to the table by the window - he’s given up trying to get Luke to number his tables. He pours the coffee and ignores the patron’s request for some Splenda and retreats back behind the counter. He pulls  _ A Moveable Feast  _ out of his back pocket. 

The bell rings and he hears Lorelai’s voice before he sees her enter. “Luke, I need coffee, stat,” she laments, throwing her purse down on the counter and plopping down on one of the stools. “Immediately. I’m coding.”

“You know coding means your heart has stopped, right?” Luke says, shooting Jess a look when he notices that he didn’t put the coffee pot in its designated place. 

“I know that - hello, I’ve watched ER. But I think my heart is in actual danger of stopping if you don’t pour me coffee right now. Or, like, inject it into my bloodstream.”

Jess snorts from behind his book. Lorelai glances over at him, expression unreadable - no doubt she’s been instructed to hate him. 

To his relief, she looks away, grinning and thanking Luke excitedly when he gives her her coffee. She takes a sip and places the mug back down on the counter.

“So, Rory left for her trip yesterday,” Lorelai says, glancing over at Jess for a millisecond. Jess pretends not to hear her, but listens intently anyway. 

“Oh, right,” Luke says with a nod. “Where is she going again?”

“The Big Apple.”

Jess snorts again.

Lorelai turns her attention to Jess with a raised eyebrow. “Should I be taking my comedic genius on the road or something?”

“I wouldn’t quit your day job.”

“Right.” She sips her coffee and then cocks her head to the side, looking at Luke. “She’s gone for the rest of the weekend, though,” she continues. “So you’ll only have to deal with one hungry Gilmore girl every morning.”

“What did you tell the parents?” Luke asks.

Lorelai shrugs. “Emily and Richard Gilmore were thrilled that Rory is getting more involved at Chilton. I, on the other hand, had to withstand a myriad of questions about my love life, job, et cetera.”

Jess shifts a bit. His eyes are on the page, but he’s not registering any of the words. He stands still, hoping that Lorelai will say something else, add anything about Rory.

“And how’d that go over?”

“No fallouts yet.” Lorelai shakes her head. “You’d think they’d want to know more about Rory or something. You know, stuff she hasn’t told them. Instead of grilling me over things they already know just so they can give me a hard time for it. Sometimes it gets to the point where I’d rather go back to how we used to be - Easter, Christmas, but nothing more. Or maybe they could take a really long vacation.”

Luke makes a noise in acknowledgement. “Well, that’s family for ya. Can’t live with them without going insane, but probably can’t live without them.”

“Hear, hear,” Lorelai agrees half-heartedly. She draws circles around the base of the mug with her finger, apparently deep in thought. “I’m a little worried about Rory, though,” she admits, her eyes flitting to the side briefly. 

Luke frowns. “Did something happen?”

“No, no, it’s just...” She hesitates. “She hasn’t said anything about it, but I can tell that something is off. Mother-daughter thing, you know?” Lorelai lets out a sigh. “She’s upset about something. And I have a feeling what it is, but she keeps denying it, so I just...I don’t know how to help her.”

“It’s Rory, right?” Luke says. “She’s gonna be fine. She always knows how to work things out.”   
“Not everything. Not this.” Lorelai purses her lips together and shakes her head. “She’s really beating herself up for something that happened recently, but she won’t do anything to fix it.”

Jess turns the page, although he hasn’t registered any of the words he’s read since Lorelai walked in. He doesn’t know Lorelai all that well, but she has to be doing what he thinks she is, right? Rory definitely didn’t put her up to it, that he can be certain of. Well, if Rory wants to fix things, it’s up to her. He’s done trying to fix things. She’s made up her mind to hate him, and there’s nothing he can do to change that. 

“Well, thank you for being the equivalent of a confessional for a minute,” Lorelai says weakly, grabbing her purse and standing up. “I have to go to the inn, make sure Michel isn’t having his third meltdown of the week or something. Oh, and Sookie asked me to tell you that your eggs benedict could use more black pepper.”

Luke glares at nothing in particular. “Give her my worst, would you?”

Lorelai does a finger gun in Luke’s direction before turning and walking back out the door. Jess sets his book down on the table, feeling an odd sense of nostalgia that he can’t quite place. Luke glances over at him, and Jess looks away quickly, muttering something about homework and ducking behind the curtain.

Intent on finding a distraction, he fishes his cell phone out of his pocket and dials her number.

**

They walk down to Times Square. Rory doesn’t mind it, it’s only about a twenty minute walk and she’s never really got to  _ experience  _ New York before. Sure, she went to the Bangles concert, and she’s been shopping with her mom there a few times, but there’s something to be said for walking around and taking note of everything you see.

It’s when they get closer, though, that things start to jump out of her. She remembers that phone call with Jess, god, it feels like ages ago, and she remembers how he told her about the sheer amount of scaffolding and the ridiculous number of trashbags on the sidewalks because they don’t have alleys. Right across from the restaurant is the Majestic Theater, and Rory remembers Jess telling her about how he only got to see one show when his mother was dating a Broadway actor, right before he left and took all their money. She remembers how he told her he still has the  _ Chicago  _ playbill with the autograph. 

It feels strange to walk these streets and think about Jess as a kid, at eight, ten, twelve, fourteen. To picture him buying a hot dog at a stand she passes or sitting on the fire escape of a building they walk by. It feels a little  _ The Only Living Boy in New York,  _ but she can’t get him out of her head.

So, not running away, just running, in any direction, because all roads seem to lead back to him, anyway.

**

She stands in front of a big glass building. The New York Times. She feels like she’s dreaming, and maybe being a little dramatic, but this  _ is  _ her dream, and it’s right in front of her. 

Inside, she looks around.  _ Someday, _ she thinks.  _ Someday, I’ll get here.  _

**

“You good?”

Jess pauses buttoning his shirt and nods. He’s been quiet for the past few minutes, he knows, but what is there to say?

Zoey pulls on her socks, taking her time in replying. She’s sitting on the chair at her desk, watching him shrewdly. “Good. You seem a little…”

“A little what?”

She hesitates. “Like you’re not all there.”

Jess scoffs, but his lack of an actual response is all too telling.

“Does it have anything to do with she who must not be named?” Zoey offers, carefully.

“Whatever happened to cigarettes after sex?” Jess mutters.

Zoey rolls her eyes. “You’re such a guy.”

“I thought that was the point.”

“You’re acting like a  _ dude.” _

Jess lets out a laugh. “A dude?”

“Yeah,” Zoey says firmly, arms across her chest. “A dude. You know, guys who only care about three things: sex, getting drunk, and not talking about their feelings.”

“Hey, I only care about two of those things.”

Zoey gives him a look. “Jess.”

“Everything is fine,” he insists. “Okay?”

She nods, but looks unconvinced. “Good work today,” she says suggestively.

Jess laughs. “Don’t be a  _ dude.” _

“Yeah, well.” Zoey hops off her chair and grabs something from her desk. “Oh, wait, before you go, I have something for you.”

He raises an eyebrow.

She hands a book to him. “Take this away from me,  _ please,”  _ she begs dramatically. “I read it and I hated it.”

“Seriously?” Jess asks. “You hated  _ On the Road?” _

“It’s so boring,” she complains. “There isn’t even a plot!”

He shakes his head in exasperation and pockets the book. “It’s  _ Keruoac.” _

“Cry me a river, build me a bridge, and get over it,” Zoey retorts crossly. 

“This is rich coming from the girl who is obsessed with  _ Titanic.” _

“Hey! That movie is a classic.”

“Yeah, classically annoying.”

Zoey moves to kick him in the shin, but he dodges her attack. “What’s your problem with it?”

“Are you kidding? ‘I’ll never let go, Jack!’” He imitates, earning another attempted kick from Zoey. “It’s incredibly mockable.”

“And you’re obsessed with  _ Trading Places,  _ so I guess we’re even.”

Jess  _ tsks  _ and shakes his head. “You’re just digging yourself a deeper grave.”

“Make sure they give me a really big headstone,” Zoey deadpans. “But that movie is so weird.”   
“It’s hilarious!”

“You probably only like it because of the scene where Jamie Lee Curtis is topless.”

Jess glares at her. “I am not that tasteless.”

“Whatever,  _ dude.” _

“How about  _ National Lampoon?” _ Jess offers.

“Which one?”

“Anyone. Vacation.”

Zoey hesitates. “Alright, that one’s fun. But isn’t Chevy Chase an asshole?”

“All those comedy guys are.”

“Fair enough.” Zoey pauses and looks at Jess again, brow furrowed. “You’re sure you’re doing okay? You know, with everything with…” The unspoken name hangs in the air.

Jess swallows and nods. “Everything’s fine. I promise.”

**

Rory can’t fall asleep. She tosses and turns and if Lorelai were there she’d definitely earn a kick in the leg, but she’s wide awake, and she can’t blame it on the jet lag. 

Finally, she’s had it. She pulls herself out of bed and sits down at the desk, grabs some of the stationary and a pen, and begins to write. 

**

Jess knocks on the doorframe, peering into Mr. Medina’s classroom. The teacher looks up and smiles, gesturing for Jess to come in.

“I, uh, wanted to turn in the writing assignment you gave me,” Jess says, getting straight to the point. He pulls the papers out of his messenger bag and sets them on the desk. “And I wanted to thank you for giving me the opportunity to save my grade. You didn’t have to do that.”

Mr. Medina removes the binder clip and thumbs through the pages. “I’m very interested to hear what you have to say here,” he says, setting the paper back down on the desk. 

“Yeah, well…” Jess scratches the back of his neck. “I also wanted to, uh...publish it. In the lit mag. Anonymously.” 

His teacher raises his eyebrows in surprise. “I think you’re making the right decision, Jess,” he says gently. “People might enjoy your writing more than you’d expect.”

Jess can’t imagine he’s right, but dammit, what does he have to lose?


	22. Paradise Lost

**Summary for the Chapter:**

> Rory attends the Chilton fundraiser, where a relationship comes to a close.

**Notes for the Chapter:**

> I'm posting. Again. I somehow wrote this at lightning speed and here we are!!!

In the end, she decides not to put the letter in Jess’ locker.

Spilling out all her feelings into a letter may have been cathartic at the time, but Rory knows that if she lets him read this letter, she’ll regret it. It’s funny - she’s constantly torn between having too many things to say or having nothing to say at all. 

Sometimes, though, it’s better to hold back. To pace yourself, to second guess, to check again, just in case. She doesn’t want to do something she’ll regret - it could just be part of her charm, but it’s who she is nonetheless. 

People say hindsight is a bitch, and maybe it is. Or maybe it’s just a way to avoid taking the blame, to say that you couldn’t have known, so there’s no point in beating yourself up over it. It’s an easy out. Hindsight is a bitch, but that’s not all there is to it. 

Rory’s dodged a couple bullets in her lifetime, this letter included, without having to put the blame anywhere. But other times, it’s not so much getting shot by a bullet as it is getting hit by a train going 200 miles an hour, and she’s all too aware that it’s all on her. 

So, in retrospect, hindsight, whatever you want to call it, Rory’s painfully aware that she should have paid attention. She should have acknowledged the signs a long time ago and saved herself all the trouble and heartache that she’s dealing with now.

When it comes down to it, she simply should have known. It’s as simple as that.

**

“Oh, honey, you look so pretty,” Lorelai gushes, hands on her daughter’s shoulders as she admires her handiwork. “And I have to say, I outdid myself with that dress.”

Rory glances in the mirror, unable to quell the fluttering sensation in her stomach. She feels like she ate a bunch of butterflies. “It’s really pretty,” she agrees. “Thank you, mom.”

Lorelai smiles. “It’s no skin off my back. Now, do you want the red lipstick, or the one that’s barely any different from your natural color and might as well be chapstick?”

“The second one,” Rory says, giving her mom a look. “What? Red lipstick is very bold and mature, and I just don’t think I’m there yet.”   
“Not Vicious Trollop?” Lorelai pouts, holding up the lipstick in question.

“What?”

“That’s what it’s called.”

“You’re kidding.” Rory takes the lipstick from her mother and looks at the bottom. “Huh. I guess you’re right.”

“That’ll teach you to question me,” Lorelai scolds, wagging her finger at Rory. “Hey, how bad of a stroke do you think your grandmother would have at this name?” She asks after a moment, looking back down at the lipstick.

“Show it to her and find out,” Rory offers.

Lorelai grins. “That’s my daughter. Now, hair up or hair down?”

Rory hesitates. “Half up,” she decides.

“Your wish is my command,” Lorelai jokes. She grabs the brush from the dresser and turns Rory around so she’s facing the mirror. They’re silent for a moment before Rory exclaims in pain.

“Ouch!” 

“Sorry, you’ve got a big knot right there,” Lorelai says apologetically. “But stop moving, or you’re gonna end up with a bald spot.” 

Rory mumbles something under her breath but stays still.

“So, are you excited for tonight?” Lorelai asks, taking a bobby pin from between her teeth. Rory nods. “Not too excited, I hope. I know necking with a boy in the backseat of his car is very appealing-”

“Oh, my god!”

“-but you don’t want your baby’s first words to be ‘automatic, systematic, hydromatic.’”

“It’s  _ greased lightning!”  _ Rory adds.

“Exactly.” Lorelai steps back to marvel at Rory’s hairstyle. “Maybe I should quit my job and go to beauty school or something.”

“Give me a call when Frankie Avalon starts singing to you.”

“Will do.” Lorelai smiles as Rory turns around to look at her mother. “Well, I’m not turning in my teasing comb quite yet, because you look gorgeous.”

Rory blushes. “Thanks, mom.”

“I simply speak the truth.” Lorelai winks before frowning. “Wait, now I want to watch  _ Grease.” _

“After I get home?” Rory offers, admiring her outfit in the mirror. While she’s never really been one to focus on physical appearance, she has to admit, a nice red dress can really do wonders for your confidence. 

“Sounds like a plan. Which will be no later than eleven,” her mom adds sternly, pointing the hairbrush at Rory. “No falling asleep with boys in dance studios, you hear?”

Rory bites her lips and nods, feeling her face go warm. Lorelai doesn’t pay much mind, already moving onto the next thing. “Okay. Do you have everything you need?”

“I think so.” Rory opens up her purse and goes through her things. “I’ve my book, my cell phone, and some money, just in case…” She frowns. “Crap. I’m out of tissues. And mints.”

“Oh, I’ve got you covered on mints. Just check my nightstand drawer. I’ve got a decade’s worth of them that I’ve stolen from restaurants.”

“Mom!”

“Relax, kid. It’s probably more like five years.”

Rory rolls her eyes. “I’m still out of tissues. I guess I have time to run over to Doose’s before Dean picks me up…”

“Do you really need any?” Lorelai asks. “You’re not sick, and unless someone is cutting onions, there won’t be a whole lot of crying.”

“I like to be prepared,” Rory argues. “Besides, if I get them now, I won’t forget about them later and then not have any when I need them.”

Lorelai sighs. “Can’t argue with logic like that. But don’t mess up your dress. Oh, and wear your sneakers. Trust me, you’ll thank me later.”

“I’ll be right back,” Rory promises, already pulling on her socks and lacing her shoes. “If Dean gets here, just tell him I’m getting something last minute.”

“Will do,” Lorelai promises. “Oh, and get some Twinkies if you can. We’re out.”

“We had a full pack two days ago,” Rory scolds her. “But fine. I will. Just pace yourself next time.”

“No promises!”

**

Rory hurries over to Doose’s and makes quick work of tracking down the tissues and Twinkies, also grabbing a few other things to restock. She moves to the next aisle over, hoping to find some bandaids, but before she can, she finds Jess instead.

She freezes. It takes a moment for him to notice her, but when he does, the surprise is evident in his expression, and she’s sure it mirrors her own. Neither one of them moves, and Rory is torn between wanting to run away without another word and wanting to see how this will play out between them.

Jess blinks a couple times in surprise. “You look nice,” he says suddenly, voice a little hoarse.

Rory’s heart skips a beat. “Thank you,” she replies, bewilderment evident in her tone even to herself.

He smiles a little. “Going to the dance?” 

“Yep,” Rory says with a nod. 

“And the shoes are, what, a statement?” He asks, gesturing towards her sneakers.

Rory frowns for a second. “What - oh. I won’t wear these to the dance, I just didn’t want to walk over here in heels.”

“Makes sense.”

They’re quiet again before she asks, “what are you doing tonight?” at the same time he says, “I should get going.”

She laughs a little. “You go.”

He shakes his head. “No. You go first.”

“What are you doing tonight?” Rory repeats. “You know, instead of the dance.”

Jess shrugs. “Not much. Might hang out with Zoey.”

“Oh.” Rory glances away, the moment broken. “Sounds fun.”

“Depends on if I have to watch  _ Titanic  _ or not.”

“Top ten most mockable films ever,” Rory supplies.

“Oh, totally.”

They lock eyes, and Rory blushes, at a loss for words.

“How have things been?” Jess asks, catching her off guard. 

“Things have been good.”

“With...Dean?”

She hesitates. “It’s going well.”

“And New York?”

“It was good,” she breathes, ignoring the fact that she never told him she was going on the trip. She can wonder about that later. Right now, she’s staying focused on the present. 

“I’m glad. Not everyone has a good experience there.”

She nods, remembering the time they talked about the Bangles concert and how her mom tracked down Madeline and Louise. The memory is painful, and she swallows, trying to push it away. “What were you gonna say?”

He shakes his head. “Nothing important. Just that I should get going. I don’t want to hold you up or anything.”

“Oh. Okay,” she says, not fighting it. “Goodnight, Jess.”

He looks back at her and smiles. “Goodnight, Rory.”

There’s a pain in her chest as she watches him leave, her shoulders heavy with what might have been. 

**

Dean picks Rory up in his car soon after. When they arrive at the venue, he holds the door open for her and puts his hand on the small of her back as they walk in. At the beginning of their relationship, she would’ve been blushing and in awe of how much of a gentleman he is. Now, she just feels crowded.

The ballroom isn’t much different than the last one, except this time there’s a table selling raffle tickets and there’s a buffet instead of servers. 

After they check their coats, Dean extends a hand. “Wanna dance?”

“Sure,” Rory agrees. She takes his hand.

He puts his hands on her waist and she wraps her arms around his neck, but the closeness isn’t what it used to be. She feels stiff and awkward, and even though his warmness should be comforting, it isn’t. (Besides, she’s getting a bit of a stretch in her arms in this position. Since when was he so  _ tall?) _

Rory wants to say something, anything, but she finds herself stumped. The two of them have barely said a word to each other the entire night, but she doesn’t know what she can say. It isn’t easy to talk to him, not like it was in the beginning.

Luckily, he breaks the silence first. “It’s bigger here. Than the last dance.”

“Oh. Yeah, you’re right.”

They fall quiet again. 

“Let’s get some food,” Rory offers suddenly. For a second, she worries Dean will be mad, but he just nods and steers them towards the buffet. 

After getting their food, they take a seat at an empty table. Something is off tonight. Something is off, with him, with them, but she cannot identify what. Not for the life of her. 

“How’s the chicken?” Rory asks weakly a few minutes later. The silence is starting to unnerve her.

Dean shrugs. “It’s fine,” he says, mouth full.

She nods and looks back down at her plate. She’s had a few bites, but she doesn’t seem to have much of an appetite tonight.

“And the pot roast?” Dean asks, remembering his manners a beat too late.

Rory shrugs. “It’s okay. I’ve had better, though, at my grandparents’. Their cook - or, I guess, the cook at the time, they never have the same cook - made it. They never have the same maid, either, but that’s another story. Whoever the cook was when we had pot roast, they did a really good job, because it was - it was good.” She takes a breath so she doesn’t pass out. 

Dean gives her a sort-of smile to acknowledge her ramble before turning back to his plate. Well, at least he’s liking the food. Whatever will keep him there. 

“Well, don’t you two look like you belong on the cover of a Nicholas Sparks novel.”

Rory looks up to see Paris and lets out a sigh of relief. “Hey, Paris.”

Paris doesn’t wait for an invitation and takes a seat on Rory’s other side. “You’re Dean, right?”

“Yeah,” Dean says, not sounding all that pleased. “So, you two are getting along now, huh?”

“I’d say that’s accurate,” Rory confirms, taking another bite of her food. Could taste better. “Rooming together twice can do that to you.”

“You’re the least worst roommate I’ve ever had,” Paris adds.

“Aw, Paris, you’re making me blush!”

There’s something resembling a pout on Dean’s face as he eyes the two girls. “So, what’s Rory like at school?” He asks, making conversation. “She was leaving Stars Hollow High when I moved there, so I never got to see her in action.”

“She’s annoyingly intelligent,” Paris replies with a wave of her hand. “Knows every answer, gets an A on everything. It’s obnoxious.”

“Thank you? I think? Or am I supposed to be offended?” Rory wonders. 

Dean nods, a slight smirk on his face. “She’s cute, isn’t she?”

Paris glances over at Rory and then back at Dean. “Is this a trick question?”

“There was this one time-” Dean leans in, expression lighting up a bit, “-I was coming over to hang out, and Rory told me to come next door. And before I could even come in, she walks out the door in this - this big peach dress with a hoop skirt, an apron, and  _ pearls.”  _ He laughs. “She’d made dinner and everything. You were pretending to be Donna Reed, right?”

“Yeah, but-”

“She basically acted as a housewife for the night. It was nice, don’t get me wrong, but kind of ridiculous looking, you know? I could never picture Rory as a housewife, but it was a sweet gesture.”

Rory’s face burns bright red as she stares down at her plate. It shouldn’t be embarrassing, but it is, and she furiously swallows down the lump in her throat.

“Excuse me,” she mumbles, standing up abruptly and hurrying away, not bothering to look back.

**

Rory takes another shuddering breath, staring at herself in the mirror and struggling not to break down. She needs to stay composed for another hour, and then - but he’s driving her home, so make that an hour and a half, or an hour and forty-five minutes if there’s traffic.

She looks at her smudged mascara and her red cheeks and notices the way her hair is coming slightly undone. She looks the way she feels - horrible. This whole night, from the drive to the food to the dancing is just that. It’s horrible. 

Everything she’s been trying to ignore about Dean is coming back up. The way he speaks to her, about her, the story he was just telling to Paris. Embarrassing her so casually, as if he was stating the weather report. 

Her mom was right. This whole time, she was right, because oh, god, Rory  _ does  _ feel unsafe and uncomfortable and he isn’t right for her, he hasn’t been in a while, but she ignored it. And for what? What was it all for? She hasn’t been happy with him in months. She tries to think of one moment, just one, but she can’t.

The bathroom door opens and Paris steps in cautiously. “Rory?”

Rory blinks a couple times. Everything is just a little blurred. “Paris?” She sniffs. “What are you doing in here?”

“I followed you. Are you...no, scratch that, you’re definitely not okay. Obviously.”

“Gee, thanks,” Rory mutters, turning back to the mirror. Big mistake - she wants to cry all over again.

Paris steps closer, ignoring Rory’s objections as she takes out Rory’s bobby pins and begins to fix her hair. Rory stands there helplessly, unsure of what to do.

“Don’t worry about that little stunt he pulled back there,” Paris begins as she works, brow furrowed in concentration. “We’ve all done stupid things for boys, and hey, if you could cook an entire meal like he said, then kudos. Takes a lot of patience, something I don’t have. There.” She steps back.

Rory manages a small smile. “It looks nice,” she says, her voice still a little choked up. 

“Of course it does,” Paris agrees briskly. She takes some paper towels and then grabs Rory’s face and turns her towards her.

“Ouch!”

“Oh, woman up.” Paris dabs under Rory’s eyes, cleaning up her mascara with the paper towel. “Do you need anything? I can go all Kamikaze on his ass if you’d like.”

Despite the situation, Rory lets out a quiet laugh. “You don’t need to do that. This is enough.”

“Then talk.” Paris wets the paper towel and then continues working. “I can listen from time to time, you know, even if my reputation precedes me.”

Rory swallows. “My mom warned me,” she says after a moment. “She noticed all the signs when I was too naive to notice them. I told her that she was wrong, over and over, and yet...here I am, in the bathroom, trying not to cry. I just...it’s all wrong,” she says, her voice cracking. “All of this. This isn’t how first loves are supposed to go.”

“Hey, cupid never released a how-to book or anything.”

“I know, but I always thought it would be different. Better.” Rory sniffs again. “That I wouldn’t be scared of his reactions or have to walk on eggshells all the time. But that’s what happened, and I just...I feel stuck.”

Paris throws out the paper towel and then hands Rory some foundation from her purse. “Go light with this, you’re paler than Snow White,” she instructs. “You’re not stuck, Gilmore. You’re intuitive. You know what you have to do.”

Rory accepts the foundation and does as Paris tells her. “What’s that?” She asks quietly, handing Paris the foundation once she’s done.

“Break up with him,” Paris says, gentler than usual. 

Rory sighs. “I don’t know if I can.”

“You’re not happy with him. It’s the only logical solution.”

“Don’t get all Spock, please.” Rory shakes her head. “I should. I know I should. I know it’s unfair of me to keep stringing him along, especially when-” She cuts herself off. “Especially when I have feelings for someone else.”

Paris nods grimly. She doesn’t look surprised. “So, what’re you gonna do?”

Rory lets out a humorless laugh. “God, I just wish that - that it could be like last time. That Jess will show up, and it’ll just - I don’t know. But…”

“But?”

“You’re right.” Rory lets out a shuddering breath. “I have to end it.”

“I can do it for you,” Paris offers. “You dodge the bullet, and I get some excellent practice in. It’s win-win. Well, except for him.”

Rory shakes her head. “I’ve dodged enough bullets lately. I have to do it.”

“Okay.”

“So, I better…” Rory glances at the door, dread building. “I should…”

Paris nods. “You got this, Gilmore.”

Rory makes her way towards the door, but when she puts her hand on it to open it, she freezes. “Thank you, Paris.”

“Hey, anytime.”

Rory smiles, takes a shuddering breath, and pushes open the door.

**

She rehearses it in her head as she walks back over to the table. With her hair and makeup fixed, she feels emboldened, but of course her bravery starts to fade when she approaches him.

“Hey, Dean,” she says, getting his attention. “I’m, uh, I’m getting a little tired. Do you mind if we go home?”

He frowns, hesitating, and her heartbeat picks up speed as she waits. “You sure you want to go?” 

Rory nods, hoping she doesn’t seem too desperate. “Please.”

He glances back at his plate for a moment. “Sure,” he says finally, but she doesn’t relax just yet.

“Thank you,” she says in a small voice, shrinking as he stands up to his full height. “I know you didn’t really want to go, and this was probably just a waste of time, since it’s only been, like, an hour, but-”

“It’s fine,” he says. “Really.”

She nods, rubbing her arm and looking away.

“Let’s get our coats.”

She nods and follows him to the coat check. His frown doesn’t go away as they get their coats, thank and tip the attendant, and walk outside. She relishes the chill in the air, the cold almost refreshing.

After a moment, Rory starts to make her way towards the parking lot, but Dean stops in his tracks and grabs her wrist, causing her to stop.

She turns towards him as he drops his hand. “Dean, what-”

“What’s going on?” He more or less demands, and Rory flinches. “You’re acting all squirrely and weird. Something’s up.”

She swallows, trying not to panic. “Dean, please, if we can just go-”

“No,” Dean says harshly. “No, you need to tell me what’s going on.”

“Dean-”

“Rory. C’mon.”

“If we could just talk later, when we get home-”

“No, tell me now, there’s no reason to wait! What are you-”

“I want to break up!” She suddenly exclaims. “I want to end this. Us.”

Dean blinks in surprise - evidently, he did not anticipate this. Then, his eyes narrow, and Rory’s heartbeat stutters at the sight. “You want to break up,” he repeats, cooly, evenly. Dangerously, even.

Rory nods. Too late to back out now. “I do.”

Dean scoffs, looking around them in disbelief. “You can’t be serious.”

“Dean, please, can we talk about this at home?”

“No. We’re going to talk about this, right here, right now.” Dean scoffs again. “I don’t believe this.”

“Why not? Things have been weird between us lately, I know you’ve noticed, and I just - I don’t want what I wanted before.”

“You’re being irrational,” Dean snaps. “It’s been a long day. You’ll feel different in the morning.”

“No, I won’t,” Rory insists. “Dean, I know how I feel, okay? Trust me on this - it’s not fair to you if we keep dating.”

Dean’s expression turns darker. “And what’s that supposed to mean?”

_ Shit.  _ Rory closes her eyes and takes a breath. “It means that I don’t want to be with you, Dean. Not anymore.”

“But you want to be with someone else.”

“That doesn’t matter,” she says patiently. “Whatever I feel, it’s different now.”

“Is this about Jess?”

She hesitates. “Kind of,” she says finally. “But it’s mostly about you.”

He’s at a loss for words for a moment, still in disbelief. “But Rory, I  _ love _ you,” he says forcefully, desperately, and she almost gives in.

Almost.

Rory takes a breath, locking her eyes with his and standing her ground. “It’s over, Dean,” she says.

Dean stands there for a moment. Then he turns around and walks away towards his car. She watches him get in and drive away, but she’s not hurting in the way she expected. She’s stranded, but she feels steadier, lighter, in a way. 

Is this what it feels like to fall out of love? It has to be. The way she feels, it’s different now. It’s been like this for a while. She just didn’t want to admit it.

She’s never really been good with firsts - her first kiss, her first love, even her first breakup. His words still echo in her mind:  _ I love you.  _ She never even got to say it when it was true, and the realization makes her want to laugh. What a strange thing, when the feeling is gone before you can ever call it by name.

Rory is unsure of how long she’s been standing there, but the wind is starting to bite and the shock is starting to fade. First things first, though, she needs to get home.

**

Lorelai pulls up in the Jeep, concern etched in her face. Rory climbs into the passenger seat, feeling oddly numb.

Lorelai hesitates for a moment before rubbing Rory’s arm comfortingly. “You okay, honey?” She asks softly. There’s something about the way she says it that makes Rory break.

She cries the rest of the way home. 


	23. A Heartbreaking Work of Staggering Genius

**Summary for the Chapter:**

> Jess' story is published in the lit mag. He and Rory have another confrontation, but nothing appears to be solved.

“Do you want to talk about it?”

Rory lifts her head from her mother’s lap and shakes her head. “No. I don’t know. I just...it…”

“It might help.”

“I don’t want to wallow. I do  _ not _ want to be that girl that falls apart over a breakup like this,” Rory insists, although she has to admit, she doesn’t sound all that convincing. “I’m not that girl.”

“Being sad doesn’t make you that girl.”

“I’ve cried over enough guys this year,” she mumbles. 

“Hey, I once cried over a laundry detergent commercial. Granted, I had given birth three weeks before, but still.” When Rory’s expression doesn’t change, Lorelai sighs. “Honey, I know I didn’t like how Dean treated you, but you still cared about him. He was a big part of your life and it’s okay to grieve losing that.”

Rory wipes her eyes. “I thought showering and watching  _ Grease  _ would help me feel better, but it didn’t. I don’t think that crying more and eating ice cream will do anything.”

“There’s no easy fix,” Lorelai reminds her. “But it can’t hurt to try.”

Rory stares at her lap. “He just got so  _ mad,”  _ she confesses after a moment. “I blurted out that I wanted to break up and...it was scary,” she admits, pulling the sleeves of her sweater over her hands. “He just…it was bad.”

Lorelai sets her mouth into a hard line. “Sounds like it.”

“He told me he loved me. That was the first time he ever said it, and it just felt like…” She swallows. “...like he was just trying to get me to stay.” She shakes her head. “That’s not why people are supposed to say it. They’re supposed to mean it - really  _ mean _ it. They should just...want you to know. But no one ever says it selflessly, do they?”

“Rory…” Lorelai trails off, unsure of what to say.

Rory shakes her head. “I don’t want to talk about it anymore.”

“Okay.”

“Can we do something else?”

Lorelai nods. “Of course. Whatever you want.”

Rory ducks her head again, feeling tears well in her eyes. “Some ice cream would be okay,” she allows quietly.

Her mom laughs under her breath. “Okay. I’ll go get some.”

Rory thanks her mom and wraps the throw on the couch around her shoulders. She can’t help but wonder - did Dean  _ really _ love her? And if he did, is that just what love is? Selfish? Saying the words with strings attached? She doesn’t want love to be selfish, but she hasn’t found it to be any different. 

**

“Jess, what is this?”

Jess looks up from the cash register and out the window where Luke is pointing. “A car.”

“And what’s it doing outside my diner?”

Jess looks back down at the cash register and continues working. “So I can drive it.”

Luke stares at his nephew, perplexed. “You bought that piece of junk?”

“Is this an issue?”

“When did you-” Luke shakes his head. “Nevermind. How did you buy it?”

“It was for sale at Gypsy’s.”

“No, I mean, how did you get the money?”

Jess gives his uncle a dry look. “Seriously?”

“Yes, seriously. What, did you rob a bank or something?”

“I had the money,” Jess says, continuing to work. “My stepfather is very rich, remember?”

“Yes, but he’s not still giving you allowance.”

Jess rolls his eyes. “I got money back when I lived there and I had some left over. Plus, this is  _ not  _ a nice car. It did not cost that much. At all.”

Luke looks from the car to Jess to the car to Jess, a comical expression on his face. “And why did you buy this car again?”

Jess lets out an exasperated sigh. “Did your kindergarten forget to tell you what a car is for or something? It’s so I can get places without walking.”

“Stop being a smartass for one second, would you?” Luke runs a hand down his chin in exasperation. “Do I have to do anything with this? Like talk to the cops when they finally find you?”

“Just sign the registration. I left it in your pocket.”

“What? I’ve been wearing this jacket all day, how could you-” Luke reaches into his pocket and pulls out the form. “Huh.”

“Are we done here?” Jess asks, closing the register. “I have stuff to do.”

“Like what?”

“You didn’t answer my question.”

Luke sighs. “I guess…”

“Great. See you later.” Jess grabs his jacket and walks out the door, ignoring Luke calling after him. He walks over to his car, unlocking it and sitting inside. Luke was right, it  _ is  _ a piece of junk, but at least he doesn’t have to borrow the truck to get to school anymore.

He opens the glove compartment, looking through the CDs he’s already put in there. He’s got nowhere to go, he just wanted to get out of the diner, but a drive outside the town couldn’t hurt. He’s about to put the car into drive when suddenly his window is blocked and there’s a knock on the glass.

Grumbling under his breath, Jess rolls down the window (again, a piece of  _ junk).  _ “What do you want, cause I’ve gotta-”

“We need to talk.”

Jess winces when he realizes whose voice it is. Knowing there’s no point in arguing, he climbs out of his car and slams the door shut. 

“What do you want, Dean?” 

Dean towers over him, scowling. “What did you say to Rory?” 

“What?”

“Don’t play dumb. What did you say to her to make her break up with me?”

“Trust me, I have no idea what you’re talking about,” Jess says evenly. 

Dean scoffs. “Bull.”

“I didn’t even know you two broke up.”

“You’re telling me she didn’t immediately run to you after dumping me?”

Jess gives Dean a look. “Hey, Bozo, Rory and I aren’t exactly on the best of terms right now. What do you think?”

Dean takes a step closer. “Give me one reason why I shouldn’t hit you right now.”

“That’s not very neighborly of you,” Jess replies coolly. “Now, are we done here? ‘Cause I have places to be.” 

(Part of him wants to say “screw it” and throw the first punch, but Jess tries to remind himself of the consequences.  _ You can’t get thrown out of another home. You have nowhere else to go.) _

“She said it was because of you, you know,” Dean sneers with barely contained fury. 

Jess’ heartbeat stutters. “She what?”

“The breakup. She said it was about you.”

Jess blinks a couple times, in shock. Dean takes another step closer, taking advantage of Jess’ dazed state. 

“So why shouldn’t I just hit you? Huh?”

“Just walk away, Dean. This isn’t worth it.”

“Nothing to say? No snarky comment? Nothing?”

“Guess not.”

Dean gives Jess a once-over before relenting and taking a step back. “Fine. But watch your back, Mariano.”

“Jeez, what is this, Salem?”

Dean casts Jess a murderous look before storming away. 

Jess shakes his head, gets back in his car and puts it in drive. But even then, his hand gripping the gear shift, Jess can’t stop replaying Dean’s words, over and over.

_ She said it was about you. _

Jess laughs under his breath. First she tells him she likes him, and then she takes it back. And now this. He’s prided himself on being a loner his whole life, on never really depending on anyone but himself. So why can’t he stop this girl from messing with his head?

**

Monday morning comes around, and for once, Rory is less than thrilled to have to go back to school. She’s almost completely certain that  _ someone  _ had to have witnessed what went down between her and Dean at the dance, and the Chilton gossip mill has never been kind to her before.

As Rory walks through the iron gates, she expects people to stop and stare and whisper. Surprisingly, though, that isn’t the case.

As she walks towards the building, a boy carrying a stack of what appears to be magazines stops her.

“Copy of the lit mag?” He asks. 

“Sure,” Rory asks, and accepts one from him. He smiles and then lets her be.

Rory opens up the lit mag as she walks through the hallway. She leafs through the pages, skimming through some of the pieces. There’s a poem she particularly likes, and a short story she thinks is cute. As she reaches her locker, she goes back to the feature piece, curious to see what’s so  _ featurable _ about it. 

_ The Easy Kill,  _ by Anonymous. Interesting. 

She starts to read, but the bell rings, reminding her that she has ten minutes to get to her next class. Reluctantly, Rory closes the magazine, but she can’t shake the feeling that the words feel familiar. She just can’t quite place them.

**

Rory exits the classroom after Mr. Medina dismisses the class. He handed out new books today -  _ Villette  _ \- and there’s something about the added weight to her already heavy backpack that adds a skip to Rory’s step. 

“Hey, Rory.”

She turns around, and to her surprise, she sees Jess, hurrying to catch up to her. 

“Can we talk?” He asks awkwardly.

Rory blinks in surprise. She briefly considers ignoring him and walking away, but before she knows it- 

“What is it?” She finds herself asking, as if nothing is wrong.

“Are you okay?”

Her eyes widen. “What?”

“The breakup. With Dean. I just…” He shrugs. “I wanted to make sure.”

Rory groans. “God, I  _ knew  _ people were talking about it! Great. What’s the rumor this time?”

“No, no, it’s not-” Jess cuts himself off. “That’s not how I know.”

“Oh.” Rory frowns. “How  _ do _ you know, then?”

“Dean.”

“You two are talking now?”

“More like  _ he’s  _ talking and subjecting me to it,” Jess mutters. “He cornered me yesterday.”

She grimaces. “Oh.”

“Yeah.” Jess folds his lips, hesitating. “So, are you? Okay, that is.”

“I guess,” Rory replies. It’s strange, them talking like this, like there aren’t any hard feelings between them. She’s confused, but it’s better than yelling, so she leaves it be. “Thanks.”

Jess nods and goes silent for a moment. Finally, he says, “Also…”

“What?”

He fidgets with the strap of his messenger bag absentmindedly. “He said...something, and while it was probably just a lie to give me a hard time or something, I thought I might as well ask.”

“What did he say?”

He takes a breath. “He said that you told him that the breakup was about me.”

Rory’s stomach drops about twelve stories. “Oh.”

“Any idea what that was about?”

“Well...I - he was really mad, and - when I was breaking up with him, he was asking - and I told him, I told him that-” She winces. “That…”

Jess looks at her expectantly.    
“He made it up,” she lies, stomach churning when a dark shadow crosses his face. “I never said that.”

“Right. Of course not.” Jess laughs under his breath. “It would be kind of unfair if you had said that, so I guess we’re all the better for it.”

“I-” Rory’s brow furrows. “Why would it be unfair?”

“Oh, please,” Jess scoffs. “Are you really asking that?”

“Yes,” Rory insists, feeling increasingly frustrated.

“At the ski lodge, you tell me you  _ want me.  _ Then a few weeks ago, you tell me that you never actually had feelings for me. Not to mention, blaming everything that went between us on me and deciding that we were never friends...it would kind of be a jerk move if you then broke up with your boyfriend because of me. Or if you said it just to hurt him.”

Rory stares at him, at a loss for words. Jess smiles coldly when she doesn’t respond. 

“That’s what I thought.”

“You’re not just an innocent victim in all this,” Rory says cooly. “You’re just repeating the same fight over and over.”

“And that’s just the same old argument.”

“Why do you even care if I told him that?” Rory demands. “It’s not like you were ever into me to begin with.”

Jess’ eyes narrow. “Like I said, it wouldn’t be fair. And besides,  _ you _ were the one who decided I didn’t have feelings for you. I never said that.”

She gapes at him. “So you do? ‘Cause if that’s the case, then you have no right to say that I’m being unfair! You should’ve spoken up the first time. But you didn’t. So either you didn’t like me, or your feelings just weren’t strong enough for any of it to matter.”

It’s Jess’ turn to be speechless as he stares at her helplessly. 

“What the hell do you think you’re even doing?” Rory yells, catching her second wind. “You hurt me, and then you parade around with that  _ girl  _ right after we-”

“Her name is Zoey,” Jess spits. “You know that. And my relationship with her is absolutely  _ none  _ of your business. You want the best of both worlds - you want me to pine after you, but you also want me to be cold and heartless so you can feel sorry for yourself. I can do whatever the hell I want with Zoey.  _ You  _ made the decision to leave me out of your life. You made your bed, so lie in it.”

“I’m surprised you have time to think about any of this with Zoey’s head plastered to your face all the time,” Rory shoots back. 

“Oh, get over it!” Jess shouts. “Yes, I’m with Zoey. Move on.”

“I could care less about you being with her. I’m just saying that you don’t need to show off with her just to try to make me feel bad.”

“Why would I do that when you’ve made it perfectly clear that you don’t care?”

“I-” Rory huffs. “I’m tired of this, Jess.”   
“Did you ever stop to think that you weren’t the only one who’s hurt?” Jess asks, voice a little quieter. 

“Why would you be hurt?” She asks, albeit admittedly, it’s a stupid question. 

“I don’t know. Maybe I’m just an easy kill.”

Rory opens her mouth to speak, but his words register in some part of her brain. An easy kill. Where has she heard that before?

Before she can connect the dots, someone else clears their throat.

“You two,” Headmaster Charleston says. “My office. Now.”

Rory looks over at Jess, whose expression has hardened. The two of them follow the headmaster, Rory’s face turning bright red when she feels everyone’s eyes on her and it dawns on her that their fight was  _ very  _ public. 

“Sit down,” Charleston instructs them sharply once they’ve entered his office, closing the doors behind him. Rory scurries over to one of the chairs in front of his desk as Jess takes his time.

Once they’re both seated, Charleston removes his glasses and runs a hand down his chin. “Never in my life,” he begins, “have I witnessed two students screaming at each other in the corridor the way you two were just now. This is a dignified institution. You don’t have to like each other, that is none of my business; however, you will  _ not  _ desecrate the halls of this school with immature squabbles such as this. Do I make myself clear?”

Rory nods and stares at her lap. Jess nods curtly and doesn’t move a muscle otherwise.

The headmaster folds his hands in front of him on his desk. “Now. Tell me, what is this fight about?” When neither Jess or Rory say a word, he sighs. “Oh, goodie, I get to guess. Let’s see. Perhaps one of you stole the other’s book or something. Or perhaps it’s a bad breakup, or something along those lines.”

When Jess flinches, Charleston nods knowingly. 

“Ah. I see.” Pause. “Whatever is going on between you two is none of my business, and I do not particularly want to know in the first place. Whether you work it out or not, I do not want to have to call you two in here again. Alright?”

Rory nods again, too afraid to look over at Jess.

Charleston sighs again. “Miss Gilmore, I’ll let you off with a warning. You have only had one additional - er -  _ incident, _ but if this happens again, there will be consequences.”

“Thank you,” Rory says in a small voice.

“Mr. Mariano, on the other hand…” Charleston turns his gaze to Jess. “I have been patient with you. I have let things slide. I warned you the last time you caused a disruption, that I would not be lenient. Does a week’s worth detention seem unfair to you?”

“No,” Jess mutters through grit teeth. “Sir. It doesn’t.”

“Good.” Charleston leans back in his chair and looks at the two. “You may leave.”

Rory mumbles a thank you and hurries out of the office, her face burning red. She doesn’t look back to see if Jess is following; she wants to be as far away from him as humanly possible.

It’s only when she gets to her next class that she realizes -  _ The Easy Kill  _ was the title of the featured short story in the lit mag. She pulls it out of her bag, and skims through the story again. It still feels familiar. 

She can’t definitively prove this theory, but she’s got a gut feeling that the story might be Jess’. And truth be told, she’s not quite sure what to make of that.

Jess wrote a story. Something changed in him since everything between them went down, and he  _ wrote a story.  _ She doesn’t want to be happy for him, but there’s a sense of pride that she just cannot shake. 

**

A couple days later, Jess gets to school early. The halls are welcomingly empty this early in the day, he notes, give or take a few students. He finds Mr. Medina’s classroom fairly quickly and knocks on the door frame.

Mr. Medina looks up from a stack of papers he’s pouring over. “Come on in, Mr. Mariano.”

Jess nods in acknowledgement. He pulls up a chair and sits down in front of the desk. “I’m not bothering you, am I?”

“Not at all,” Mr. Medina assures him. “Actually, there’s something I wanted to let you know, so your timing is just short of perfect.” 

“How so?”

“Your story has been  _ very _ well received by the student body,” Mr. Medina tells him happily. “Not only have I heard your peers talking about it or even telling me, but your teachers enjoyed it as well. Mrs. Ness was particularly moved by it.”

Jess fidgets uncomfortably, unsure of how this makes him feel. “Huh.”

“I’m proud of you,” Mr. Medina says, and suddenly, Jess feels the urge to cry. “You’ve come a long way since September.”

“It’s not that big of a deal.”

“Oh, I disagree. You’re passing the class now, Jess, and you’re coming into your own as a writer. I knew you had it in you.”

“Yeah, well…” Jess shrugs. “Just didn’t want to flunk out, I guess.”

“Which you wouldn’t have cared about in September,” Mr. Medina says. “And your story...you’ve got a future as a writer. Keep pursuing it. And I’d consider submitting another one for next month’s issue, too.”

“That’s actually what I wanted to talk to you about.” Jess reaches into his messenger bag and takes out a stack of papers with a binder clip at the top. “I...I wrote another. And I was thinking, and I’d be okay with publishing this one, too.”

Mr. Medina takes it from him and smiles. “I’d say that’s a good decision.”

“Save it until you read it,” Jess mumbles, but Mr. Medina shakes his head. 

“None of that, okay? I’ll make sure to include this one, anonymously if you want-”

“Actually,” Jess says, cutting him off, “put my name on this one. Please,” he adds as an afterthought. 

Mr. Medina raises his eyebrows in surprise. “Are you sure?”

Jess nods. “Yeah. I am.”

“Okay.” Mr. Medina sets the papers down on the side of his desk.  _ “Dear Mister K,  _ by Jess Mariano. I like the sound of that.”

“That’s all I wanted to talk about, so if you’re busy, I-”

“I want to speak for a little longer, if that’s alright by you,” his teacher interrupts.

“I’ve got nowhere else to be.”

Mr. Medina hesitates for a moment before he speaks. “You’ve read  _ The Catcher in the Rye,  _ I assume?”

Jess blinks in surprise. “Yeah.”

“Figured as much. So, you know the scene where he speaks to his old teacher?”

Jess nods again. “Mr. Antolini.”

“Right. ‘This fall I think you're riding for - it's a special kind of fall, a horrible kind. The man falling isn't permitted to feel or hear himself hit bottom,’” Mr. Medina recites. “You’re not Holden Caulfield, obviously; however, you’ve had a rough go of it lately. And I’ve done my best to make sure you have support, but…”

“But?”

He sighs. “I worry about what you’re going to do after you graduate Chilton. I don’t want you to fall off the face of the Earth.”

“My stepfather always assured me I’d get a job wiping tables or refilling gas. I’ll be fine, don’t worry.”

Mr. Medina doesn’t laugh. Instead, he purses his lips together, looking tense. “‘So they gave up looking. They gave it up before they ever really even got started.’ I don’t want that to be you, Jess. But the reality is that with your grades, you won’t be accepted into any of the prestigious universities, I’m afraid.”

“I wouldn’t want to go to them anyway,” Jess says, but Mr. Medina doesn’t seem to hear him.

“Community college is not a bad option. But I think you should continue with your education after you graduate.”

Jess fidgets uncomfortably. “I get it, but...school isn’t really for me.”

“Still  _ do _ something with your life, Jess,” Mr. Medina argues firmly. “If you don’t want to go to college, that’s your decision to make. But keep writing, learning...and most importantly, keep  _ trying. _ Okay?”

Jess swallows. “Okay.” He isn’t quite sure what else to say. 

“That’s all I had to say,” Mr. Medina says gently. “But thank you for putting up with this somewhat incoherent lecture. It’s important to me that you hear this.”

“Thank you,” Jess manages to choke out. “I...it does mean something to me. That you care.”

“Of course. You’re not a lost cause, Jess. Far from it, in fact.”

Jess nods and stares down at his lap, his teacher’s words hitting harder than most. Keep trying. He thinks he can do it, but part of him wonders, what would be the point? He did it for Rory, at first, and now, he doesn’t really have anyone at all.

But he thanks Mr. Medina and exits the classroom all the same, trying to ignore the odd sensation in his chest. Trying. He doesn’t exactly want to fall off the face of the Earth, either. But is trying enough? Is that really all it takes? 

Probably not. But Mr. Medina, for some reason, believes in him. That alone makes Jess start to think it might actually be worth it to put in his best effort and  _ try.  _

**

On his way to last period, Jess catches a glimpse of Rory on the top of the stairwell as he makes his way down. Their eyes lock briefly, but Jess quickly diverts his gaze. Rory’s gaze lingers for a moment before she turns away. The both of them keep moving, walking away from the remnants of their friendship, of whatever there was between them before it all fell down. 


	24. Catch-22

**Summary for the Chapter:**

> Tensions come to a head at Louise's house party.

**Notes for the Chapter:**

> While it's a long one - a little over 7k words, jeez - this chapter is probably one of my favorites so far. I hope you all enjoy and/or feel other things.

“Rory.”

Rory’s head shoots up from behind her copy of  _ White Teeth  _ by Zadie Smith, which just arrived the night before, much to her excitement. “What do you want, Louise?”

“Are you doing anything tomorrow night?” Louise asks. 

“Not really. My mom wanted to rewatch our recording of  _ Who Wants to Marry a Multi-Millionaire,  _ but that can always be postponed. Why?”

The corners of Louise’s mouth curl up as she takes a piece of paper from her binder and hands it to Rory. She looks down at what appears to be a flyer for a party. 

“I’m hosting a party tomorrow night while my father’s on trial,” Louise explains in her signature drawl. “The jury had to be sequestered, so I have the whole place to myself for a while. Perfect opportunity to throw a party, don’t you think?”

“Oh, well...I guess,” Rory stammers lamely, frowning down at the flyer. “Why are you inviting me? I thought you guys hated me or something.”

“No, that was only when Paris hated you,” Madeline chimes in. Rory acknowledges Madeline’s response with a sarcastic smile. 

Louise smirks. “Everyone’s invited, even you.”

“I’m flattered,” Rory deadpans. “What’s with the personal invite, then? If everyone’s invited I’m sure I would’ve caught wind of it from Hedda Hopper or Louella Parsons eventually.”

“Well, then I wouldn’t have been able to shoehorn you into going, then, would I?”

“I guess not. But seriously, why do you even want me there?”

“Consider it an olive branch,” Louise explains. “I think this is the beginning of a beautiful friendship, don’t you?”

“I wouldn’t have pegged you as a Casablanca enthusiast.”

Madeline scrunches her face in confusion. “Casablanca? Is that the one with the umbrellas?”

Rory shakes her head. “Nevermind.”

"So?” Louise prompts. “Are you going?”

“I don’t know. These things really aren’t my scene.”

“My mom is getting us a keg,” Madeline offers. 

Rory folds her lips to keep back a laugh at the absurdity of Madeline’s comment. “I don’t drink.”

“Of course you don’t. Hey, you could bring your boyfriend - the gorgeous one that was six-two?” Louise cocks her head when Rory glances away at her words. “You two didn’t break up.  _ Really?  _ That’s a shame. He really was gorgeous.”

Rory fidgets uncomfortably. “I’ll think about it, okay?” She holds up the flyer. “But don’t get your hopes up. I think I’d survive even if I missed out on ‘music, moonshine, and more.’”

Louise smirks. “I’ll look forward to seeing you there.”

“That slogan was my idea. Bye, Rory,” Madeline adds sweetly, before she follows Louise down the hall.

Rory looks down at the flyer. Her curiosity just might get the best of her, and besides, her mom has been encouraging her to get out and have fun after the breakup. She could invite Lane or something, dress up, make a day of it. She probably won’t go, but she folds the flyer up and slips it into her backpack, just in case.

**

Rory steps out of the stall and turns on the faucet. She stifles a yawn, dreading returning to her class - as much as she loves to learn, she’s willing to bet she’d survive without any math in her life.

As she washes her hands, the door swings open and Zoey steps in. Rory quickly looks down at her hands, attempting to hide her face, but Zoey still catches a glimpse of her in the mirror and waves.

“Hey, Rory,” she greets her, as if their last interaction hadn’t happened. 

“Hey, Zoey.”

“We’ve got to stop meeting like this,” Zoey jokes.

Rory remains silent, turning off the faucet and ripping some paper towels out of the holder to dry her hands. Zoey watches her for a moment, frowning.

“Are you going to Louise’s party tomorrow?” 

Rory shrugs, still not making eye contact. “I’m not sure,” she answers, tone cold.

Zoey nods slowly. “Alright. Just...thought I’d ask. Make conversation and all that.”

“It’s a bathroom. We don’t need to talk every time we run into each other in one,” Rory snaps. She feels a little guilty when Zoey’s face falls, but she turns away quickly to hide it.

Eager on getting out of there as soon as possible, she moves towards the door, but Zoey calls out, “Rory, wait.”

Rory stops and turns. “What?”

Zoey rubs her arm awkwardly, hesitating before she speaks. “I know you don’t like me. And that’s okay. I just...I want you to know that I’m not a bad person, and that I don’t hate you, even if you seem to hate me. I hope that someday you’ll warm up to me, but if you don’t, that’s fine, too. I can’t force a friendship here or anything.” She smiles weakly. “That’s all I wanted to say, so you can go now.”

Rory grimaces. “Zoey, wait.”

She looks over her shoulder at Rory expectantly. 

“I don’t...I don’t hate you. It’s not that. It’s…” 

The unspoken name hangs in the air between the two girls, and Zoey seems to understand perfectly. 

She smiles somewhat sadly and nods. “Good. I’m glad. Just...don’t be a stranger, you know?”

Rory purses her lips together and nods. Zoey steps into a stall and latches the door shut behind her, effectively ending the conversation.

Rory exits the bathroom, face a little flushed. Zoey always seems to catch her off guard, but she’ll chalk it up to bad luck - and while she feels slightly guilty for her attitude towards the other girl, Rory just can’t help herself. She knows, she  _ knows  _ that she’s being unfair, but  _ fair  _ would be still having Jess in her life, but right now, Zoey has him instead. 

It’s enough to make a girl a little bitter. 

**

“She  _ hates  _ me.”

Jess glances up from his book from his perch on her desk. “She doesn’t hate you.”

“She does,” Zoey insists, twisting closed a nail polish bottle and reaching for the other. “I mean, she claimed she didn’t, but her and I both knew she was lying.”

“Trust me, she saves all the hate for me.”

Zoey stops mid-twist and puts the nail polish down. “You know why she hates me, right?”

Jess looks at her warily. “No, but I’m sure you’ll enlighten me.”

“It’s because she’s jealous.”

“Of who?”

“Don’t act stupid,” Zoey reprimands him gently. “You know what I mean.”

“I really don’t.”

“Do I have to spell it out for you?”

He nods, eyebrows raised.

“She’s jealous because she wants to be with you.” Jess scoffs, but she holds up her hand to silence him. “Come on, Jess. You’re observant, and most of all, you  _ know _ her. You’re honestly telling me you haven’t noticed?”

“It doesn’t matter.”

“And why is that?”

“Whatever I felt for her…” Jess shakes his head. “I’m over it. All of that is in the past.”

Zoey cocks her head to the side. “Are you sure?”

“I didn’t have a choice,” he says quietly. “She made it very clear that she was never into me in the first place.”

“Hey, girls lie all the time,” Zoey argues, and Jess snorts.

“You know, a guy could really fall for a girl just by hearing that.”

“Oh, shut up. And stop deflecting.” Zoey opens the top-coat. “Open your eyes. She’s in love with you, you  _ idiot.” _

“The name calling was uncalled for.”

“Whatever. You’re impossible.”

“Yes, that is my reputation.”

Zoey picks up a nail polish bottle and mimes throwing it at him, to which he rolls his eyes at.

She sets down the bottle. “Truce?”

“Just keep waving that white flag.”

“Hey, did you hear about Louise’s party?” She asks suddenly. 

Jess shrugs. “In passing. Didn’t think much of it. Why?”

“We should go!” Zoey exclaims. He laughs. “What? What’s so funny about that?”

“I’m just not really the party type,” Jess explains, still laughing. “Can’t we just...stay in?”

“Just for a little bit. C’mon!”

“No.”

Zoey pouts. “You suck.”

“Can’t you go alone?”

“What would be the fun in that?”

“I’m sure you can think of something.”

“What do I have to do to get you to go?” Zoey begs. 

“And why do you even want to go so badly?”

She sighs. “It just seemed fun, I guess. I’m a bit of an extrovert.”

“How we get along, I’ll never know,” Jess says, shaking his head. “Look. We can go for an hour  _ tops. _ But after that, I’m leaving with or without you. Deal?”

“Deal!” Zoey exclaims excitedly, to which Jess groans. “You won’t regret it. I’ll make it worth your while.”

“Oh, yeah?”

She smiles knowingly before looking back at her feet. “I think I did a good job. When do you need to be home again?”

“Eleven.”

“So, we’ve got a little while,” she says suggestively. Her gaze flickers to the nail polish and then back to Jess, a devious smile starting to spread across her face.

“No,” he says before she can get a word out. 

“Come on, you didn’t even consider it!”

Jess stands up and grabs his jacket off the chair. “I’m leaving. I’ll pick you up at eight tomorrow.”

“Spoilsport!”

He flips her off before closing the door behind him. 

**

In the end, Rory decides to go to Louise’s party.

Lorelai was ecstatic when Rory returned home with the flyer in tow. “You have to go and tell me everything that happens,” she’d exclaimed. “It’s been a good sixteen years since I went to a high school party. Ooh, tell me if they still play Elvis Costello, would you?” So, Rory agreed to go, figuring she’d spend an hour or so there making casual conversation before driving back home. 

The night of the party, Rory stares at her closet, unsure of what to wear. She could go jeans-sweater-sneakers, but that might be too casual. She could wear a dress, but would that be too nice? Her boots might go with that skirt well, but-

“How about this blouse?” Lorelai asks. Rory yelps in surprise and nearly jumps out of her skin. 

Lorelai holds her hands up in mock surrender. “Jeez. I swear, I come in peace.”

Rory blushes. “Sorry. I didn’t hear you coming.”

“I have been working extremely hard on my stealth skills,” Lorelai quips. “But seriously. What do you think?”

“I don’t know if I can pull it off.”

“Don’t be ridiculous,” Lorelai scolds. “Wear it with that skirt you wore to dinner last night and that jacket with the patches and your docs and you’re golden.”

Rory reaches into her closet and pulls out the jacket in question. She holds it up beside the lilac blouse and squints. “How do you do it?” She exclaims, shaking her head. “You just put together an outfit in point-two seconds.”

Lorelai smiles. “Hey, can I do your hair?”

“Please do.” Rory bites her lip in concentration. “How about like we did it for the Bangles concert?”

“I like the way you think, Coco,” Lorelai says with a gleeful grin. 

Once Rory has dressed, agonized over whether to wear tights or not, and scrutinized the outfit in the mirror for the customary ten minutes after the “yes!” verdict on the tights, Lorelai sits her down and starts to do her hair. It feels a little too much like the previous week, when they were sitting in the same position to get ready for the dance. But Rory resolves to put on a brave face and just keep going. She’s cried, she’s grieved, and now, it’s time to move on. 

After picking out lip gloss and giving herself one last once-over in the mirror, it’s time to go. Lorelai had agreed to lend her the Jeep for the night, as she had decided to stay home and take the opportunity to watch all the movies Rory hates and eat the sushi that makes Rory nauseous. 

“Have a good time, hon,” Lorelai says before planting a kiss on the top of her daughter’s head. “Be home by twelve.”

Rory agrees, certain that she’ll be home much earlier than midnight. But she thanks her mom again, promises not to do anything Lorelai would do, and closes the front door behind her on her way out. 

**

Rory can hear the thudding of the bass as she pulls up and parks in front of the large brick house. She double checks the address just in case, although admittedly, it isn’t very necessary. Still, it’s good to make sure, just in case. 

The volume of the music increases by about a thousand percent as soon as Rory steps through the threshold. She takes a breath and steels herself before walking any further. She wishes Lane were here and not stuck at home under the watchful eye of Mrs. Kim - she could do with a little backup.

She makes her way through the throng of people, looking around for a familiar face. So far, she doesn’t see anyone she can particularly place. Word really got out about the party - the room is packed. 

“Rory!” Rory spins around to see Madeline and Louise, both dressed up and holding red solo cups. “You came! And you look good, too - I love the shirt. Where’d you get it?”

“My mom’s closet?” Rory suggests weakly. “Thanks, though.”

“Vintage,” Louise notes. “Very nice. Eighties?”

“Impressive.”

“I tend to have a good eye for these things.”

“Apparently.”

“Are you having a good time so far?” Louise implores. “I’m trying to get a read on how people are enjoying this party so I can make notes for the next one. Each one  _ has  _ to be better than the last.”

Rory shrugs. “I won’t be much help. I just got here.”

“Let me know later, will you?” Louise asks, her eyes already tracking a guy from their history class. “I have to make the rounds, but feel free to wander. Just don’t go into the master bedroom. Oh, and the drinks are over there.”

“We’ll see you around,” Madeline adds with a smile. The two girls wave before moving on.

Rory glances over towards the keg and the other drinks and decides to get some punch. She’s thirsty, and the idea of some punch  _ is _ very appealing. 

She pours a cup and brings it to her lips. She takes a small sip, but the aftertaste is a bit off. She takes another sip before realizing the punch is  _ definitely  _ spiked, suddenly choking on the drink and coughing furiously.

“Oh, that is  _ definitely  _ spiked,” she hears a familiar voice say behind her. She turns around, still coughing, and finds herself face to face with Paris. 

“I didn’t think you’d come,” she manages to choke out.

Paris rolls her eyes. “My mom said I had to stay until 10:30. I’m counting down the minutes, trust me.”

Rory wipes her mouth and casts a disdainful look at the red solo cup in her hand. “Why would they spike the punch? There’s already beer!”

Paris smirks at Rory’s perceived innocence. “It’s a high school party, Gilmore. I wouldn’t trust any liquid that isn’t unopened and sealed tightly.”

“What’s in it?” Rory frets. “Is it a lot of alcohol? Will I be able to drive home?”

“Calm down,” Paris snaps. “You’ll be fine. You took the smallest sip I’ve ever seen anyone take in my life.”

“I feel lightheaded. Am I supposed to be lightheaded?”

“You’re overreacting.”

Rory scrunches up her face and throws her cup away. “That’s it. I’m never accepting a drink from anyone, ever.”

“Give it a rest, Bambi.” 

“I am  _ not-” _

“Wait, look who just walked in,” Paris interrupts. Rory follows her gaze, and to her surprise she sees Jess walk through the main doors, Zoey by his side. 

“James Dean decided to make an appearance with blonde Natalie Wood.”

Rory can’t look away from Jess as he pushes past multiple people, ignoring their objections. She watches as he nears her and Paris, feeling frozen to the spot.

Zoey greets Rory with a smile that feels a little artificial before turning to the drinks table and taking a soda. She hands another to Jess, who glances over at Rory, and the two of them stare at each other until Zoey takes a sip of her soda and says, “let’s go.”

Jess nods and wraps an arm around her as they walk off. He looks over his shoulder for a moment, but glances away quickly. 

Something in her snapping, Rory turns back to the punch and grabs herself another cup. Pretending she doesn’t have the sudden urge to sob, she takes a large sip, ignoring the burning and the bad taste. Paris watches her with wide eyes, but when she opens her mouth to comment, Rory gives her a warning look.

“I’m gonna go look around,” she mutters before turning her back on the punch table and walking away.

**

Rory walks through the hallway, passing a few of her classmates who are leaning up against the walls and talking. She’s only had a few more sips of the punch, but she feels kind of warm inside and a little more relaxed, which she has to admit is a welcome feeling. 

Out of the corner of her eye, she catches a glimpse of a head of curly blonde hair. She turns around slowly, just in time to see Zoey and Jess laughing before ducking into a bedroom and closing the door.

Rory stares at the door, fighting back the tears that are now pressing up against her eyes. Jealousy is a monster, she knows, but maybe she can keep it at bay for a little while. She makes her way back to the drinks and refills her cup.

“Screw it,” she mutters, and takes a big swig from the cup.

**

Ten to however many minutes later, and Rory knows that she is  _ definitely  _ drunk. She’s starting to feel a little drowsy, and, shit, she isn’t sure how she’s going to get home, but she’s liking the way she’s able to push thoughts of Jess away, so she keeps on drinking the punch. 

She’s lost track of how long she’s been wandering, saying hello to people she recognizes from class and peering inside some of the rooms off the hallway. Turning the corner, she narrowly misses someone, and starts to lose her balance out of surprise.

Before she can fall, a hand grabs her wrist and steadies her. 

“Oops,” she says with a giggle, a noise she’s surprised to hear herself make. She looks up, and her eyes widen when she sees that the hand that caught her belongs to Jess. 

His eyes narrow as he looks her over. “You’re drunk.”

Rory scrunches up her face and shakes her head. “Nope. Not drunk.”

“Is that the punch?” He asks, gesturing to her cup.

Zoey takes the cup from Rory and sniffs it. For confirmation, she hands it to Jess, who does the same. “Yeah, you’re  _ definitely  _ drunk,” Jess repeats.

“You might wanna get her home,” Zoey tells him, glancing back at Rory.

Jess stares at Rory for a moment, concern etched in his face, before nodding. “Yeah.”

“I don’t need to go  _ home,” _ Rory objects. “I’m fine. I’m not even that drunk!”

“How many cups have you had?”

She pauses to count them out on her fingers. “Two and a half.”

“Yep. I’m taking you home. How did you get here?”

“Drove.”

“You still have the keys?”

Rory opens her purse and pulls them out. “Keys,” she says in confirmation.

Jess looks at Zoey. “Go,” she encourages. “Call me when she’s home and safe and I can take your car over to get you.”

“Fine,” he allows, taking his keys from his pocket and handing them to Zoey. “Alright,” he says, turning his attention to Rory. “Come on. Let’s go.”

Rory pouts, but she allows him to take her arm and pull her through the crowd. “I know how to walk,” she protests, but he ignores her. However, they don’t make it very far at all, because who else but Tristan approaches them, a dubious look on his smug face.

“What’s going on here?” 

Jess holds her arm a little tighter. “Nothing. Now go away.”

Tristan, however, steps closer, curious. Rory scowls and looks away from him.

“Oh. I get it. You’re trying to find a place to...I get it.” Tristan smirks. “Wait, aren’t you screwing that Zoey girl, too?”

“I’m taking her home,” Jess says through grit teeth. “This really isn’t any of your business, so I’d advise you to fuck off before you do something you’ll regret.”

“Oh, a  _ threat.”  _ Tristan  _ tsks.  _ “Well, in that case…” 

Jess tries to step past him, but Tristan blocks their exit. “Come on,” Jess mutters. “You cannot seriously be doing this.”

“Is she drunk?”

_ “She  _ has a name, you know,” Rory pipes in defiantly, but it just makes Tristan laugh under his breath. 

“She’s a bit of a handful. Trust me, I know this from experience. I can take her off your hands, if you want,” he says, and moves to take Rory’s arm, but Jess gives him a shove to keep him away.

The look on Tristan’s face turns from cunning to furious as he advances on Jess. Rory watches in horror as he swings his fist and punches Jess in the face. Everyone around them goes quiet and turns to watch as Jess pulls himself up.

“What is wrong with you?” Jess growls. 

“What’s wrong with  _ you?”  _ Tristan counters. “Why are you even helping her? I thought you two hated each other.”

Jess scoffs. “Fuck off. It isn’t any of your business.”

“You made it my business when you just waltzed into my life a year ago,” Tristan spits, venom dripping from his voice. “No one wants you here, Jess,  _ no one.  _ Not even her. You just come in and leech off of everyone around you no matter who it hurts.”

“What on Earth are you talking about?”

“You know  _ exactly _ what I’m talking about. My father barely even acknowledges my existence, and it’s your fault. You and your mother enter our lives and suddenly it’s ‘Jess-this’ and ‘Liz-that.’ And then when she died, it was all about that.”

“My mother fucking  _ died  _ and you’re making it all about yourself. Unbelievable.”

“Everyone here was better off before you came here,” Tristan snarls. “Everyone.”

Jess’ hands curl into fists, but he takes a few evening breaths to steady himself. “Rory, let’s go,” he says, grabbing her arm again and marching out of the house before the fight can escalate any further. 

Once they’re outside, Jess eases his grip on her arm. He looks wild and a little scary in the moonlight, she thinks. 

“Where’s your car?” He demands more than anything. 

“It’s my  _ mom’s  _ car,” she corrects him sternly. “I don’t have my own car.”

“Great. And where is it?”

She just shrugs.

Jess grumbles under his breath. He swiftly uses the keys to locate the car, which, of course, is right in front of them. He glares at her, but she just looks at him innocently, so he shakes his head and unlocks the car.

Jess helps her into the passenger seat and makes sure that she’s buckled before climbing into the driver’s seat. She has a lot of questions, mostly about Tristan, but the look on his face keeps her from asking any of them. He puts the key in the ignition and starts to drive. 

About ten minutes into the drive, Rory starts to feel ill. “Jess,” she moans, tugging at his sleeve. “I don’t feel well.”

“You think you’re gonna be sick?”

She nods. Jess lets out a sigh. “Okay. Hold it until I can pull over.”

“I’ll try.”

He pulls over as quickly as he can. Rory promptly stumbles out of the car and gets sick in some bushes. Jess hesitates before getting out of the car and walking over to her. She feels his hands brush against her neck as he holds her hair back, waiting for her to finish.

Rory straightens up, legs shaking, and wipes her mouth. “Sorry,” she mumbles.

Jess just shakes his head and helps her back into the car without a word. He buckles, but he doesn’t start the car. There’s a black eye forming where Tristan punched him, she notices, and it makes her stomach turn to even think about. 

“Why were you drinking?” He asks. He won’t look at her. “It’s so not you to do that.”

Rory stares down at her lap, fidgeting with her hands. She feels a little better, a little less drunk, but her heart is still aching in her chest and she feels a little lightheaded. “I don’t know.”

“There had to have been a reason.”

She doesn’t say anything. 

“I know you. You wouldn’t just decide to drink for the hell of it.”

“Hey, maybe I’ve changed since we were friends,” she argues.”

Jess’ jaw clenches. “Not that much.”

“You don’t know.”

“Rory…” He trails off, his voice slightly hoarse. “Why have you been acting off these last few weeks?”

Rory bites her lip. “I don’t know,” she murmurs. “I don’t really remember.”

“Rory.”

Hearing him say her name so softly hits a nerve, and she squeezes her eyes shut to hold back any tears that may spill. “I don’t want to talk about it. If I talk about it, then...then I have to deal with all these feelings that I really, really don’t want to deal with.”

Jess finally forces himself to look at her. His brow is knit together, and something about him looks softer, a little less guarded than usual. “Is it about Zoey?”

She nods.

Jess exhales slowly, leg bouncing slightly. “You were done with me, Rory,” he says quietly. “What did you want me to do?”

Rory swallows. “I don’t...I don’t like you with her. I don’t like it at all.”

“Why?” 

She takes a deep breath before speaking. “I know I can’t have you all to myself, but...I don’t want you with anybody else, either.”

After a moment of silence, Jess clears his throat. “We should...we should get going so your mom doesn’t get worried or anything”

Rory nods and doesn’t argue. “Okay.”

He puts the car in drive and gets back on the road. They’re both silent for the rest of the drive.

**

Jess pulls up in the driveway of Rory’s house and parks. He glances over at Rory; she’s been looking a little better since she got sick, but she’s been nodding off for the past few minutes. He nudges her.

“We’re here.”

She blinks and straightens up, drowsy. “Where?”

“At your house.”

“Oh.” She unbuckles slowly and opens the door, but stumbles a bit in climbing out. “Jess, I need your help,” she calls, and Jess grumbles under his breath before getting out of the car.

“Come on,” he mutters, hooking his arm in hers and pulling her away from the car and towards the house. She stumbles beside him, eventually coming to a stop. 

“I’m tired.”

“Well, I’m not carrying you, so you’re gonna have to deal,” Jess counters. She pouts, but when he wraps an arm around her waist to steady her instead, she doesn’t object.

Finally, they make it up the stairs and to the front door. Jess fishes her keys out of his pocket, but there’s an absurd amount of keys, and it would take way too long to go through every single one, especially in this lighting, so reluctantly, he knocks on the door.

Lorelai’s voice grows louder as she approaches the door. “Kirk, I told you, I don’t want any girl scout-” She goes silent when she opens the door. “Woah, what the hell happened to you two?”

“I had some punch,” Rory pipes up. Lorelai frowns, no doubt piecing it all together. 

“It’s a long story.” Jess takes a deep breath, bracing himself from Lorelai’s inevitable freakout. “She’s a little drunk, so I took her home.”

“Come on in,” Lorelai says, surprising him. There’s a worried look on her face as she looks at her daughter, but no anger to be detected. At least, not towards him. 

Lorelai relieves Jess from keeping Rory upright, and leads her daughter as far as the hallway, where Rory pushes off of her and rushes to the bathroom to get sick again. Lorelai sighs and presses a hand to her temples. 

“You did the right thing by bringing her here,” she says sincerely. “Thank you.”

“No biggie,” Jess replies with a shrug, but Lorelai shakes her head. 

“How much did she have to drink?”   
“Uh, I’m not sure. I wasn’t with her all night.”

“So you were doing other things during this party, which begs the inevitable question - what the hell happened to your eye?”   
“Nothing.”

_ “That _ doesn’t look like nothing.”

They hear the toilet flush, bathroom door click shut, and the shower turned on. Lorelai turns back to Jess and hesitates for a moment. “Take a seat.”

“I don’t-”

“Just sit down, kid.”

Figuring it’s not worth it to fight, Jess takes a seat at one of the chairs at the kitchen table. Lorelai opens the freezer and takes out an ice pack. 

“You just have those on hand?”

“Don’t underestimate my clumsiness,” Lorelai chastises him playfully. She sits down. “There’s a lot of injuries in the Gilmore house, mostly involving coffee table legs and my toes. Now hold still.”

“What-”

Lorelai presses the ice pack to the side of his eye. Jess manages to hold back a noise of surprise, mostly. He wants to push her away, but her grip on his shoulder is tight and she’s got this super-focused look on her face that he’s admittedly a little wary of crossing her. 

“So who gave you this shiner?” She asks after a moment.

“This kid named Tristan. You probably don’t-”

“Oh, I know Tristan,” she says, laughing under her breath. “The kid’s a real winner, isn’t he?”

“Oh, you have  _ no  _ idea.”

She smiles a little as she holds the ice to his eye. “Here. You take over. Be careful not to touch the eye itself or anything.”

Jess wordlessly accepts the ice pack from her and holds it in place. 

Lorelai gets up and fills up a glass of water. She hands it to him, and Jess takes it, still surprised. “How do you know how to take care of a black eye?”

“With age comes wisdom, or something like that,” Lorelai advises. She leans up against the counter and looks at him shrewdly; Jess fidgets a little under her gaze. “So, you and Rory. Are you two friends again, or…?”

Jess hesitates. “She just needed help tonight. That’s it.”

Lorelai nods slowly, but she looks unconvinced. “Things have been rough between you two lately, huh?”

Jess doesn’t say anything.

“She was really hurt, you know, after everything that happened.”

_ There it is.  _ “I know,” he says quietly, jaw clenched.

“I know that what she did wasn’t a great decision,” Lorelai continues, “but I also know that Rory is a good kid. She didn’t mean to hurt you, same as I assume you didn’t mean to hurt her, either.” She sighs. “She misses you, Jess. She may not show that to you, but she does.”

Jess doesn’t know how to respond, so he stays silent, his whole body tense.

“I may look very youthful, but I’ve lived long enough that I’ve learned some things, and the two of you haven’t had the same chance. And don’t get me wrong, I haven’t always handled things perfectly - I’m sure you’ve heard about my torrid affair with the english teacher - but listen to me when I tell you that both of you are going to regret letting your pride interfere with your relationship. One of you needs to take the first step. Otherwise...you won’t get anywhere.” Lorelai claps her hands together and straightens up. “Okay, my lecture is over. You’re free to go. Use warm compresses on that eye for the next few days, okay?”

Jess exhales and stands up slowly. “Thank you,” he says quietly.

Lorelai waves a hand in dismissal. “You brought my daughter home. It’s the least I could do.”

He nods. “And...she’ll be okay?”

Lorelai smiles. “Yeah, she’s gonna be okay.”

He nods again. “Good.”

**

Zoey arrives shortly after Jess calls her. She pulls up behind the diner where Jess is waiting, leaning up against the brick wall.

She rolls down the window. “You look like you’re about to start snapping your fingers,” she calls in lieu of a greeting. 

“Maybe, but my dancing skills are a little rusty.”

Zoey smiles. She steps out of the driver’s seat and closes the door behind her by leaning against it. “So, front or back?” She asks casually. 

Jess laughs under his breath. Needing a distraction, he steps towards the backseat and slides in. Zoey gets in after him and closes the door behind her. 

Zoey climbs onto his lap and straddles him.  _ Rock ‘n’ Roll Suicide  _ is playing faintly on the stereo as she leans in and kisses him. Jess responds, his hands slowly moving to her hips. She deepens the kiss, but when her hands slide down his chest, Jess breaks apart and stops her. “Wait,” he says, breathing heavily. “Can we...can we stop?”

“Of course.” Zoey climbs off his lap and sits next to him, watching him concernedly. Jess stares down at his lap, something inside him threatening to break. “Are you okay? What’s going on?”

“Nothing. It’s just…”

Zoey bites her lip. After a moment, she speaks up, voice soft. “Are you still in love with her?”

Jess looks over at her, caught off guard. “In love? What-”

“Jess,” she says gently, “I know you’ve been denying it ever since we started doing...whatever it is we’re doing, but…” She sighs. “You said you were over her, and I didn’t want to push you too hard on that. But the way you look at her, talk about her…that’s love if I’ve ever seen it.”

Jess stares at his lap, hunched over with his hands clasped in front of him. She reaches out and strokes the side of his face, feeling how tight his jaw is set. 

“I understand wanting a distraction. I just don’t think sleeping with me is going to give you what you really want, you know?” She takes her hand back. “So...are you?”

Jess’ jaw ticks, and Zoey waits quietly for him to speak. “Yes,” he finally says, his voice hoarse. 

There’s no  _ I told you so  _ or  _ I knew it!  _ or  _ ha! _ from Zoey like there would typically be. Instead, she nods, a sober look on her face. “I think we should probably stop this, then.”

“Yeah. Probably.”

“Still friends?” Zoey asks anxiously, sneaking another glance at him.

Jess gives her a warm smile, one that actually reaches his eyes. “Yeah. Still friends.”

She grins and lets out a sigh of relief. “Good. ‘Cause I’m not quite ready to cut you out of my life.”

“Me neither.”

“Will you still drive me home?”

“Nah. I was gonna let you hitchhike, see if you’d start to appreciate Kerouac.”

“Shut up and get in the driver’s seat.”

“Yes, ma’am.”

**

Jess waves goodbye to Zoey before she slips inside her house and closes the door behind her. As he watches her leave, he realizes he doesn’t feel sad, or any sense of loss; it’s more nostalgia than anything else. He’s too worn out and tired to consider what all of this means for him and what all of this means for his relationship with Rory, so he just drives, hoping that maybe when he wakes up in the morning, it’ll all make a little more sense.

**

Rory has showered and brushed her teeth twice, but she still doesn’t feel great. Lorelai hasn’t said much, leading Rory to fret over just how angry she might be.

Lorelai checks in on Rory as she’s getting into bed. “Are you feeling better?” she asks, mouth set into a line. 

Rory nods, too afraid to make eye contact. “Yeah, a little.”

“Good. Now I can move on from being worried to being other things.”

Rory cringes. Lorelai takes a step further into the room, her arms crossed. 

“Barring any positive pregnancy tests, the last thing I want is for my sixteen year old daughter to be coming home drunk from a party.”

“I’m so sorry, Mom, I-”

Lorelai holds a hand up. “I’m not finished. You don’t do things like this, Rory. What got into you tonight? What made you think that drinking was a good idea?”

Rory stares at her lap. Despite her breakfast-themed matching pajamas, she feels very exposed under her mother’s shrewd glare. “I wasn’t thinking.”

Lorelai snorts. “Obviously.”

“I was just...I was at the party, and I got some punch, and then I realized it was spiked, so I stopped, but then - then Jess showed up, and he was with - he was with Zoey, and I hated it, I hate seeing him with her. I just...I didn’t want to have to deal with that.”

Her mom lets out a long sigh. “Seeing him with someone else is really hard on you, huh?”

Rory nods and hides her face.

“I can understand that,” Lorelai says quietly. She takes a seat on the edge of Rory’s bed, drumming her fingers against her legs. “I’m still not happy with what you did tonight, but I know that you’re a good kid, and that this won’t become a usual thing. Right?”

“Right,” Rory says firmly. 

“So just...get some sleep, okay? And  _ never  _ tell your grandparents about this.”

Despite everything, Rory smiles. “I won’t.”

“Good.” Lorelai smiles and kisses the top of Rory’s head. “Get some rest, hon.”

“Goodnight, mom.”

“Goodnight.”

The door shuts closed behind her. Rory falls asleep not long after.

**

The next morning, Rory has just about the worst headache she’s ever had. Lorelai holds back her snickers as Rory trudges into the kitchen and downs a glass of water.

“I’m never drinking again,” she groans, slumping into a chair.

Lorelai pats her on the shoulder and hands her a couple painkillers, doing her best to hide her laughter.

**

When Rory is at her locker Monday morning, she steals a glance at Jess. Something feels different than it did before the party, like the rift between them has been altered, either by repairing itself or falling apart even more. She looks away, ignoring the pang in her heart when she hears his locker door shut. 

**

When the bell rings, declaring the school day over, Rory hurries to pack up her things and get to the bus. It’s been a long day, and honestly, all she wants to do is get home, take a warm shower, and curl up with a good book. 

She’s in the courtyard when she catches a glimpse of Jess running after her. Confused and curious, she slows to a stop, allowing him to catch up with her.

“I just...need to talk to you for a minute,” he says, a little out of breath.

“What’s up?” She asks, adjusting her grip on her textbooks.

He hesitates for a moment, still catching his breath. “At the risk of repeating earlier incidents...are you doing okay? You know, after the party and everything?”

“Oh. Yeah, I am.”

“Okay. Good. I just wanted to make sure.”

“I’m good,” she reassures him. “My mom was a little upset about it, but we smoothed it over pretty quickly.”

“I’m glad,” he says with a slight smile. “And I, uh...I wanted to let you know that Zoey and I? That’s over. Still friends, but...that’s it.”

“Oh,” she says, inwardly cringing at the bright tone to her voice. “I’m, uh, I’m sorry…?” She trails off, unsure of how to react.

He shakes his head. “Don’t be. I just wanted to let you know, you know, after what you said in the car and all.”

She frowns. “What?”

“You don’t remember?” He asks, his voice faltering a bit. 

She shakes her head. “No. Sorry,” she adds quickly. 

“It’s fine. You were drunk. I shouldn’t have expected you to.”

“What did I say?” She asks anxiously. What could she have told him? Did she confess her feelings for him or something? Her heart starts to pick up as she waits for him to answer. 

“Nothing, really,” he says finally. “You were drunk and tired and just...said something about how you didn’t know what was going on with me and stuff. That’s it.”

She laughs shakily, relieved. “Okay. Just wondering.”

She expects Jess to say goodbye and walk away, but he remains rooted to the spot, hands awkwardly shoved in his pockets. “I also wanted to...to say that I’m sorry. For everything.”

Her breath catches in her throat in surprise. “Jess-”

“Wait. I just need to finish. I…” He swallows. “I should’ve said something. What I did...it wasn’t okay. You just...you caught me off guard, and all I could think was that you were with Dean and how scared I was of not having you as a friend. So I’m sorry. I didn’t mean to hurt you, but I did, and in doing that...I broke everything. I wish I could take it back, but I can’t, and now…now I just have to accept that things are different and that I can’t recover what I lost.”

She blinks a couple times, unsure of how to reply. “What did you lose?” She asks, her voice almost a whisper. 

He takes a deep breath, looking at her almost hopelessly, something that breaks her heart even more. “I lost you,” he says finally.

She can’t think of anything to say, and it’s like all her words and thoughts are gone and she’s frozen, screaming inside but with a silent exterior. When she stays silent, Jess smiles sadly, nods, and walks away, leaving her to repeat his words in her head, over and over and over.

**

As Jess walks away, heart still pounding loudly in his chest, he finds himself replaying what he said over and over, like he needs to pick apart and analyze every word of his apology that was long overdue.

He realizes, now, though, from her lack of a response, that he never really lost her. He couldn’t have. It’s a catch-22: to have lost her, he would’ve had to have had her in the first place. 


	25. Brave New World

**Summary for the Chapter:**

> Rory attends a debutante ball as a favor to her grandmother.

**Notes for the Chapter:**

> I apologize for the long wait - inspiration and motivation are a little scarce lately. Hope you all are doing well!
> 
> NOTE: some recognizable dialogue is from 2x05 of Gilmore Girls.

Rory rings the doorbell and waits patiently until Emily’s newest maid opens the door and ushers her in. Rory kindly refuses her offer to take her coat, promising that she’ll only be a minute before she leaves.

She can hear chatter from the patio out back, so Rory heads towards the noise, figuring she’ll say hi to her grandmother before grabbing her book and going. 

“Oh, Rory! What a nice surprise!” Emily greets her granddaughter with a wide smile, turning towards the sound of the door opening. 

“Hey, grandma. Sorry to butt in like this,” Rory apologizes, hanging back behind the threshold. She may be nice enough to say hello, but she’s listened to her mother enough to know that if she goes any further, she’ll get sucked into a quite endless conversation that she really doesn’t want to have to endure. 

Emily beckons for Rory to take those dreaded few steps. “Nonsense. Come meet my friends.”

Knowing she doesn’t have a choice, Rory does as she’s told, taking a few steps forward before deeming herself at a safe distance and stopping. 

“Ladies, I’d like you to meet my granddaughter, Rory,” Emily says to her friends.

“Well, hello, Rory,” one of the women says. Rory steps forward again. DAR ladies care a lot about manners, right? 

She manages a smile. “Nice to meet you.”   
“My goodness, what a pretty girl you are,” one of the women - a blonde one with short hair - says sweetly, although there’s an air to her voice that unintentionally makes Rory feel about five years old. “She looks just like Lorelai, doesn’t she?”

“The eyes!” One of the women exclaims.

“The nose!”

“Walk around, sweetie.”

“Sunny, leave the girl alone,” Emily chastises, and Rory lets out a sigh of relief. Compliments like these make her uncomfortable and she was honestly starting to feel like she was on display instead of popping by to pick up a book. 

“I want to see the walk,” the woman insists. “Lorelai had such a specific walk.”   
“Fast,” the redhead woman says. 

“That was it.”

“Come, sit,” Emily says, ignoring the other women. “Would you like some tea?”

“Oh, no, I just came to pick up a book that grandpa was supposed to leave for me,” Rory says apologetically.

“Go check his study. It might be on his desk.”

“Okay, thanks!” Rory says cheerfully. She turns away from the group of women and makes her way towards the study. Sure enough, the book is on her grandfather’s desk. It’s a thick one, definitely way too big for her to fit in her bag, so she carries it out of the room.

Figuring she ought to say goodbye to her grandmother and the DAR women, she takes a detour back to the patio. 

“I found it,” she says, holding up the book as proof. When the women just eye her with wide smiles, Rory fidgets under their gazes, unsure of what to do. “Yay,” she says weakly. They just keep staring. 

“Rory, come here for a moment, please,” Emily says. Rory obliges, but she’s starting to get a feeling that her grandmother is plotting something. “There’s something I want to talk to you about.”

“Okay…”   
“Have I ever talked to you about the Daughters of the Daughters of the American Revolution debutante ball?”

_ Oh, no.  _ “No, you haven’t,” Rory answers, rubbing her arm anxiously.

“You know, it’s very important for a young girl like yourself to be properly presented to society,” Emily begins, barely containing her smile. 

“Very important,” one of the ladies chimes in.

“It is?” Rory asks weakly. 

Emily nods. “Very much so. It’s always good for people to know who you are - in a good way, that is.”

“Well, there’s no such thing as bad press,” Rory jokes, but Emily just gives her a puzzled look. “It’s - it’s a saying. Nevermind. Anyway, you were saying?”

“Right,” Emily says, smiling widely. “It’s very important to come out to society, and not everyone gets to do it in such an extravagant way. I’m sure that if it were up to your mother, she’d throw you in the back of a hay ride with the words  _ on the market  _ taped to your back.”

“Oh, no, she’d be a lot more feminist about it.”

“There’s flowers, and music, and cake…” Emily says dreamily, her eyes almost glazed over. 

“Every young girl dreams of this day,” the redhead woman contributes with a knowing nod. 

“And let me guess, you want me to…come out?”

Emily’s grin broadens and Rory knows she got it in one. “You’d be the prettiest girl there.”

“Thanks,” Rory says awkwardly. “When, um, when is it?”

“The sixteenth.”

Rory’s eyes widen. “What? That’s next friday!”

“It’s a little last minute, I know, but trust me, they’ll make an exception for you,” Emily assures her, but it does nothing to calm Rory’s nerves. 

“Don’t you still have Lorelai’s old gown?” The blonde woman - Sunny - asks.

Emily’s eyes light up. “Yes, in fact, I do.” She turns to look at Rory, and while her first instinct is to say  _ no, thank you,  _ she catches the look of hope in her grandmother’s face and caves.

“Okay,” she says, imagining how her mom will react to all this. “I’ll do it.”

“Excellent!” Emily exclaims. “Now, do you have to be home soon?”

“I’ve got some time to kill.”

“Perfect. Let’s go upstairs, shall we? I’m sure your mother’s old dress will fit.”

Rory swallows, looking at all the ladies and then her grandmother. She can tell from the look on her grandmother’s face how important this is to her, so she manages a weak smile. “Okay. Let’s!”

**

After Lorelai gets over the initial shock, and Rory convinces her to go along with it, it’s mostly smooth sailing from there. Lane comes over later that evening, and the three girls sit on the floor by the couch, pouring over the pamphlet. 

“This actually looks kinda fun,” Lane says brightly, earning a look from Lorelai. “What? I’d love an excuse to dress up and dance without my mother finding out and calling two ministers and a pastor.”

“Ooh, that sounds like the title of a really good Jim Belushi movie!” Lorelai exclaims. 

“The phrases ‘really good’ and ‘Jim Belushi movie’ don’t exactly go together that well,” Rory points out.

“Uh, two words:  _ K-9 911.” _

“I’m not listening to the opinion of anyone who unironically enjoys  _ Dude, Where’s My Car?” _

“So, what do you need for this shindig? A dowry?” Lorelai asks, glancing at the pamphlet. “Well, you already have a dress. I guess you’ll need shoes, hose, gloves...some mice, a dog, a pumpkin…”

As her mother is talking, Rory keeps reading, not planning on encouraging her mother’s mocking. Her heart sinks, though, as she reads further. Lorelai must notice the sudden change in Rory’s expression because she frowns and asks, “What’s wrong?”

“Uh, nothing.”

“Rory.”

“I - I know. It just says that…”

“Your father is supposed to present you at the ceremony,” Lane finishes for her. 

Lorelai’s face falls. “Oh.”

“Whatever, it’s no big deal, I can get someone else to do it. Grandpa, probably-”

“Rory-”

“Or Taylor-”

“Okay.”

“Or the cable guy. Looked pretty friendly last week. Maybe he has a tux,” Rory jokes, trying to keep her tone bright, but the mood in the room has shifted. 

“Hand me the phone,” Lorelai says after a moment of hesitation. 

Rory frowns. “I was kidding about the cable guy.”

Lorelai gives her a look as Lane hands her the phone. 

“What are you doing?” Rory asks as Lorelai dials.

“Look, missy. There are plenty of things that should weird you out about coming out, but inviting your father shouldn’t be one of them.”

“He’s not going to come.”

“He might,” Lane suggests, but her attempt at a bright tone is weak at best. 

“You don’t know until you ask,” Lorelai adds.

“Mom…”

“Look. We call, we ask. There’s no harm. Trust me, the cable guy’s not going anywhere.” Lorelai finishes dialing and walks out of the room to the kitchen. “Ah! Hi!”

Once Lorelai is out of earshot, Lane turns to Rory. “You okay?” 

Rory nods. “Yeah. Yeah. It’s just...there’s another thing, too.”

“What?”

She points at part of the pamphlet. “You need an escort, too. And the boy that would’ve been my escort is out of the picture, so…”

Lane grimaces. “That sucks.”

“It’s fine. I’ll just - I can find someone else, right? It can’t be that hard - my grandma probably knows some boys, and I-” She cuts herself off. “God, who am I kidding? And was I seriously considering asking my  _ grandmother  _ to set me up?”

“Do you know anyone from school?” Lane offers. 

“Other than Paris? No. And I can’t exactly ask  _ her, _ can I?”

“I guess not. And you’re sure there’s no one else?”

Rory shakes her head. “Nope. No one else.”

“Hey, Little Debbie, your dad is definitely going to be there!” Lorelai announces as she walks back into the family room. 

Rory’s head perks up. “You’re kidding!”

“No, he’s gonna walk you down the stairs and turn you in a circle, watch you curtsy, and announce that Rory Gilmore is officially open for business.”

“I can’t believe it,” Rory marvels, grinning despite herself. “And he definitely said ‘definitely?’”

“Definitely.”

“So there’s a 50/50 chance?”

“I don’t know, he sounded pretty sure. I’d say 60/40.”

Lane grins. “Tell him I said hi, okay? I gotta get home. Mama Kim is making something soy-based for dinner. Can’t miss that, right?” She adds with a grimace.

“You’re stronger than either of us could ever dream to be,” Rory assures her. Lane smiles and waves goodbye before walking out the front door. 

Lorelai turns back to Rory with a smile. “So, what else do we need? I have a feeling we’re on a good luck streak - maybe I can convince Kirk to sell us his mime gloves.” Rory grimaces and Lorelai frowns. “Hey, that’s not the face of a girl who’s feeling lucky.”

Rory wordlessly hands the pamphlet to her mother and points at the part about the escort. She watches as her mother’s face falls as realization dawns on her.

“Oh. Honey...”

“I don’t know what to do,” Rory admits quietly. “I mean, Dean and I  _ just  _ broke up - I can’t ask him, and I don’t have anyone else. The cable guy’s a little too old for me.”

Lorelai sighs and strokes her daughter’s hair. “Don’t worry about it right now, okay? We’ll figure it out.”

“Don’t worry about it? It’s a week from tomorrow!”

“Hey, there’s a 70/30 shot that your dad is going to show up,” Lorelai says forcefully. “Let’s focus on that and celebrate instead, okay?” When Rory doesn’t reply, she gives her arm a little squeeze. “Okay?”

“Okay,” Rory gives in glumly. 

“Let’s look at your shoes, see if we have anything - if we get lucky and don’t find anything, maybe we can go shoe shopping this weekend!”

“Mom, you have enough shoes already.”

“There is no such thing as having enough shoes. Have I taught you nothing?”   
Rory shakes her head. “Nevermind. We can look and deliberately ignore all the perfectly acceptable choices so you have an excuse.”

“That’s the spirit!”

**

“So, Rory, are you excited for the ball?”

Rory glances up from her plate, finishing chewing and swallowing before she answers. “Yeah, I guess. I mean, the fan dance is a little much, but otherwise, it seems fun.”

Lorelai shakes her head. “Where did I go wrong these last sixteen years?”

“Well, I’m very glad,” Emily says with a smile, ignoring Lorelai. “I was worried that your mother would have clouded your opinion with all her over-exaggerated horror stories.”

“Well, she tried.”

Lorelai gapes at her daughter. “Et tu, Brute?”

“So, Christopher called,” Emily continues with a knowing smile. “He was considerate enough to inform me that he’s coming to the ball to escort Rory.”

“Woah, way to be underhanded, mom. And he’s only coming because Bill the cable guy is out of town.”

Emily rolls her eyes. “I’m sure it’s no thanks to you, Lorelai.”

“Actually, mom was the one who called him,” Rory interjects. 

Her grandma looks surprised, but she shakes it off. “At least he didn’t have to hear it off the street.”

Lorelai gives her mother a look. “Who would be talking about this on the street?”

“And you have everything else you need? Gloves, hose?” 

“Not yet, but we’re going to the mall tomorrow,” Rory explains before taking another bite.

“Well, don’t worry about the gloves,” Emily instructs. “We’ve got Lorelai’s old ones, and I don’t think her hands were much bigger than yours.”

“Gee, thanks, mom. I’m flattered.”   
“And get extra pairs of pantyhose, just in case.”

“Just in case of what?”

Rory laughs under her breath as her mom and grandma bicker. It dies down after a moment, Lorelai pouting but giving in to Emily’s admittedly hard-to-follow logic. 

“Rory,” Emily begins, and Rory looks up, mid-bite. 

“Mm?”

“Your mother filled me in on your...situation, regarding an escort.”

Rory’s eyes widen as she does her best to swallow without choking. “What? Mom?”

Lorelai gives her an apologetic look. 

“And I think I’ve solved your problem.”

“Again, what?”

“Well, since you’re no longer with that bag boy-”

“Mom,” Lorelai says in a warning tone. 

“-I figured I’d save you the trouble of trying to find someone.”

“You didn’t have to,” Rory says anxiously, bracing herself for the no doubt fancy and unfamiliar name of a Hartford high society boy that she’ll probably hate. 

“Nonsense. You’re my granddaughter, and I’ll do what I can to help.” Emily smiles. “I was thinking over who I could ask, and then I remembered that friend of yours that attended your birthday party back in October.”

Rory’s stomach drops in dread. The only boy she can remember her grandparents meeting is a tall, blonde, and obnoxious one, and the last person she’d want to escort her at the debutante ball is  _ Tristan.  _ “I-”

“I called him up earlier today and asked him. While his phone manners leave much to be desired, he agreed, so you will not have to worry.”   
Rory grimaces. “Oh, Grandma, you didn’t-”   
Emily looks at her, puzzled. “I thought you two were friends. You brought him up before.”

“Trust me, Grandma, I really appreciate it, but I am  _ not  _ friends with Tristan.”

Emily frowns. “Tristan? Dugray? No, I didn’t ask him.”

“What? Then who-”

“I asked your friend, Jess,” Emily says slowly. “Jess Mariano. You mentioned he was your friend earlier in the school year.”

Rory blanches at Emily’s words.  _ Jess?  _ And he  _ agreed?  _ She frowns at her plate, her head spinning. She and Jess haven’t spoken since that afternoon in the courtyard the week before. She thinks he’s been avoiding her, and honestly, she doesn’t blame him; while he caught her off guard with his words, what else could he have said when she had stayed silent? So why did he agree? He hates this world, had only just escaped it - what could have possibly convinced him to willingly step back into it, for her no less?

“Is that not alright?” Emily asks, brow furrowed in concern. “You look pale.”

Rory takes a breath and shakes her head. “It’s - it’s fine, grandma, really. Thank you.”

Emily smiles. “Of course.”

Rory stays fairly silent for the rest of the meal. She picks at her food, her appetite completely gone. She has so many questions, and none of them are ones she should ask. How did her grandmother get his phone number, for starters? And why ask  _ him?  _ Jess is the opposite of high society, someone she thought her grandmother would look down upon for sure. How much does Emily know about him, anyway? Does she know he used to live with the Dugrays, and if she does, does she know he doesn’t anymore? 

Why did it have to be Jess?

**

Rory stares at her hands in her lap, remaining silent as Lorelai gets on the highway. Her mom glances over at her, concerned.

“What’s going on in that head of yours?”

Rory bites her lip, picking at a loose thread on her coat. “I can’t believe she asked _Jess._ And how did she even get his number? They don’t exactly run in the same circles.” When Lorelai purses her lips together and doesn’t say anything, Rory frowns. “What? You’re not going to go on a tirade about how manipulative and intrusive she is?”

“Okay, first of all, I resent that,” Lorelai says. “Secondly, am I really  _ that _ predictable?”

“Mom. Really. What’s going on?”

Lorelai exhales slowly, eyes on the road. “Promise you won’t get mad?”

“About what?”

“I...I asked your grandmother to ask him. I took his number from your address and book and gave it to her. That’s how she got it.”

Rory’s eyes widen in shock. “What? Why - why did you - what-” She scoffs. “I don’t believe this.”

“Rory…”

“Why, mom? Why did you do that?”

Lorelai sighs. “Honey, I love you, but you two weren’t going to communicate unless someone pushed you to. Even after the party incident and what you told me he said last week - nothing was changing.”

“Maybe I don’t want to make amends. Ever think of that?”

“Is that true?”

Rory stares out the window and doesn’t respond.

“You two were close, hon. I’d hate to see you lose him forever.”

“I don’t think our friendship can be fixed,” Rory mumbles.

“You won’t know until you try,” Lorelai says softly. “And besides. Who knows, maybe it’ll become…more than that.”

Rory laughs under her breath. “You and I both know that isn’t going to happen.”

“He seems to care about you a lot, Rory. Even after everything that happened, he took care of you, helped you-”

“Yeah, because he’s not a bad person.”

“It’s because he cares about you,” Lorelai says firmly. “And I’m no Pauline Phillips, but still, after everything you two have been through, there’s still something there. And I know, I know you told me to stay out of this kind of thing, but I had to meddle a little, or else you two would’ve kept up acting like you hate each other and refusing to make amends.”

“And you think him being my escort will help?”

Lorelai shrugs. “I mean, you’ll have to talk to each other, dance…”

Rory groans. “Mom...this isn’t going to end well.”

“You don’t know that, hon.”

Rory sinks back into her seat, staring out the windshield. “Why would he agree to this?”

“I think you know the answer to that.”

Pause. “Do you really think…” Rory swallows. “Do you really think that he…”

“I mean, I don’t know for sure, but mothers have a sense for these things.”

“I hurt him a lot,” Rory says quietly. 

“It happens.”

“And he hurt me.”

Lorelai nods. “I know. But the question is, are you going to let the past get in the way, or are you going to set aside the proverbial pro-con lists and let yourself follow your heart for once?”

“The last time I did that, everything fell apart.”   
“Things are different now.”   
“And Dean would be mad,” Rory says quietly, making Lorelai wince. “If anything happened with Jess...he already basically threatened him.”   
“Dean isn’t your boyfriend anymore,” Lorelai reminds her. “And he shouldn’t be a factor in this. If you like Jess, if that’s who you want, then that’s what matters. Not Dean, not anyone else.”

Rory is quiet, thinking over her mom’s words. She has to admit, her mom has a point, as she tends to. Nothing was changing between her and Jess, and now with all this happening, it’s going to have to. But Rory’s still afraid. Everything is at risk, everything is on the line. One wrong move, and her second chance? It could be gone.

And yet. And yet, still, part of her is starting to hope. If Jess agreed to this, then maybe her mom is right. Maybe everything that happened was a misunderstanding, a product of bad timing. She isn’t sure if the thought is comforting or if it makes her even more worried.

She’ll just have to wait and see, which is her least favorite thing to do, but she’s learning now that with Jess, she has to adapt. He’s a shock to the system, but not in a bad way, he’s just different, intoxicating, world changing. Her life hasn’t been the same since she met him, and it hasn’t been the same since she lost him. So, maybe, things can change again.

So just this once, she closes her eyes and hopes.

**

Rory wakes up Monday morning with a sense of apprehension and dread. Maybe she should be grateful that her escort problem is solved, but all she can think about is seeing Jess at school and how undeniably  _ awkward  _ it’s going to be. 

She manages to avoid Jess throughout the first half of the day. He sits behind her in English, yes, but she stubbornly looks straight forward and refuses to turn her head for the duration of the class. She exits as quickly as possible when the bell rings, and moves briskly to her next class. She follows the same strategy through lunch, but of course, fate had to catch up with her. Or, in this case, Jess. 

She stops at her locker before her next class, trading out one textbook for the other. When she shuts her locker door closed, she’s suddenly face to face with Jess. She nearly jumps out of her skin.

“God!” She exclaims, a hand to her chest. “Do I need to put a bell on you or something?”

He laughs a bit under his breath. “Sorry. Didn’t mean to startle you.”

“It’s fine.” 

“Good, good.”   
They fall into an awkward silence. Rory looks away quickly, scratching at her arm, and Jess shifts back and forth on his feet. 

“So what did you-” She says at the same time that he begins to speak. “Sorry,” she apologies quickly. “You - you go.”

“I, uh, I wanted to talk to you. About the ball.”

Rory cringes. “I’m sorry about that. You can totally bail on that if you want, it’s fine - it was my grandma’s idea, I had no idea she was going to ask you until she told me on Friday, and by then it was too late, and I didn’t want to be ungrateful, but seriously, if you don’t want to do it, it’s fine.” She takes a deep breath so she doesn’t suffocate from lack of oxygen as she rambles. 

Jess smiles a bit at her rambling. “It would be kind of rude of me to back out.”

“Oh, like you care about manners.” She winces when she realizes how that sounds. “Sorry. I didn’t mean it like - I was trying to joke. Sorry.”

He shrugs. “No biggie. So,” he says with a small dip of his head, “this...thing. It’s a debutante ball?”

She nods. “Yeah. It’s just - it’s a coming out ball. It’s this whole thing, kind of over the top, really, but I’m doing it for my grandma. And who knows, it could be fun.”

“And I’m your…?”

“Escort. It’s like, my dad walks me down the stairs and then hands me off to y- to the escort.”

“Ah.”

“Yeah.”   
He shifts a bit so he’s leaning his back up against the lockers instead of one shoulder. “And why me? Why not some blue-blooded family friend or something?”

“What, like Tristan?”

He almost laughs. “Something like that.”

“I...” Rory swallows, unsure of how to answer. She doesn’t want to lie to him, but how can she tell him that her mom is meddling so they can have a shot at a relationship without sending him running for the hills. “My mom told her that I didn’t have an escort because of...of the break up, and she mentioned you.”

The look in his eyes is unreadable as he watches her. “Why?”

She does a bit of a double take. “Why what?”

“Why’d she mention me?”   
“Well…”

“I mean, we haven’t exactly been on the best of terms lately,” he says, slower than usual. “And you and I both know that neither of us have really made an effort to...reconnect. So why’d she think of me?”

Rory avoids eye contact, looking anywhere but at him. “I don’t know.”

“Rory.”

She takes a breath and braves a glance at him. He looks softer than usual, his guard not as high, and her heart twinges at the sight. “I think she just...she knows how much we meant to each other before...everything. And she meddles, sometimes, and I think she’s taken it upon herself to fix us.”

“To fix us.”

She offers him a half smile and shrug. “Something like that.”

He looks far away for a moment, loss in his thoughts. She waits quietly as he seems to come back to reality, blinking a couple of times to adjust. “I guess it just...it is what it is, then.”

She frowns a bit, not quite understanding what he means. “And what is it?” She hears herself ask after a moment.

“It’s whatever you want it to be,” he says after a moment. 

“What I want?”

“I’m here, Rory,” Jess says cryptically. “I’ve been here. And I’m just fine waiting. I’m not in any rush. But you need to decide. What...all this is.”

“Jess-”

“I have to get to class,” he says, cutting her off. “Am I just...seeing you around?”

“Well, we have to prepare for the ball,” she answers, but she’s still stuck on  _ And I’m just fine waiting. I’m not in any rush. But- _

“And what does that entail?”

She finds herself beginning to smile. “Do you know how to dance?”

**

“Well,  _ you’re _ graceful.”

“You stepped on my feet!”

“So I’m not a great dancer. Sue me. Sorry if I’m not Frances freaking Houseman.”

“No one’s asking you to change your name to Baby and get a nose job. Just go get a right foot and we’re set.”

Miss Patty gives the two of them a look, no doubt exasperated. “Okay, this isn’t working. Lorelai and Chrsistopher, why don’t you act as an example?”

As she starts up the music again and her mom and dad begin to dance, Rory shoots a glare in Jess’ direction. He returns it, and she elbows him in the side.

“Hey!”

“Pay attention, dears,” Miss Patty drones, but Rory is fairly certain she wants to use a much different word than  _ dears.  _

Once the music is off again and Lorelai and Christopher stop dancing, Miss Patty walks over to Rory and Jess. Jess makes a noise of protest when the older woman grabs his arm and puts it on Rory’s waist, and then Rory’s on his shoulder. “Then your hands go together like so. Now, try again. One-two-three, one-two-three…”

The music starts up again and they attempt to dance, but Rory stumbles almost immediately, nearly toppling to the floor. Jess saves her and not all that gently pulls her up by the arm. 

Miss Patty massages her temples. “Rory, honey, step aside for a moment. I’ll show you what you need to do.”

Rory willingly obliges and watches with delight as Miss Patty forces Jess to dance with her. Jess is clearly very uncomfortable, and she stifles a laugh. Jess shoots daggers at her until Miss Patty lets him go. “You got that, dear?”

“I think so.”

“Try it again.”

They get in position. When the music starts up again, they actually last a good ten seconds, until one of them missteps and they accidentally bang foreheads.

“Okay, that’s enough,” Miss Patty says, shutting off the music. “They’re helpless.”

“Give me and Rory a second, Patty?” Lorelai asks. When the other woman nods, Lorelai grabs Rory by the arm and drags her outside.

“What’s with all the manhandling today?” Rory complains once they’re outside the barn. “And by the way, it’s Rory and  _ I,  _ not me and Rory.”

“Done with the grammar lesson?” Rory glares at her mom, but nods. “Good. Look, I get that the two of you are in that cutesy bickering stage, but you gotta knock it off for a minute so you can dance without accidentally reenacting that scene from Young Frankenstein.”

“Maybe we just don’t dance well together,” Rory argues. “And besides, you remember how bad I was at ballet. I think that lack of skill transferred over.”

“Well, you’re gonna have to find a way to get past that. Otherwise your grandmother will lock us in the basement and throw away the key.”

“Fine.”

Lorelai glances back towards the barn. “How long until you think she makes him dance with her again?”

Rory folds her lips to hold back a smile. “Ten bucks says she already has.”

“You’re on, you and your talking money.”

**

The rest of the week moves by fast. Rory isn’t sure if that’s good or bad, but soon enough, it’s Friday night, and it’s almost time to leave.

She’s nervous, sure, but she also finds herself feeling a little excited. It’s not that she didn’t catch her father’s several disapproving looks at Jess or his muttering to her mother, and it’s not that she didn’t catch signs of regret etched on Jess’ face as Lorelai forces him into a tux to make sure it fits and Miss Patty makes him twirl her for the third time. It’s not any of those things - no, it’s that while her mother has taught her to be wary of Hartford high society, parts of it are still appealing, and while the fan dance is a bit much, she enjoys the dressing up and looks forward to the  _ food.  _

After Lorelai does her makeup and her hair, there’s a knock on the door, which is no doubt Jess. “I’ll get it,” Rory calls out to no one in particular - her mom is now preoccupied with a nail filer and her father is in the other room on the phone. She hurries over to the door and opens it, and there’s Jess, wearing his whole tux minus the jacket, which he’s carrying, looking a little uncomfortable but relieved when she opens the door. 

“Thank god,” he mutters. “I keep thinking I hear Babette.”

“What, don’t want her to see you in that suit?” 

He gives her an affirming look as he steps over the threshold. She closes the door behind him, following him out into the family room. Lorelai looks up from her nails and smiles in greeting. “Well, don’t we look dapper?”

“Hey, do you have a coat closet?” Jess asks, turning towards Rory.

She furrows her brow in confusion. “Yeah. Why?”

“No reason. Just was considering hiding in it until it’s time to go.”

“Absolutely not,” she says crossly. “You’re suffering through this with me.”

“Do I have a choice?”

“Nope.”

“Figured.” 

“Do you want a soda or anything?”   
Jess looks down at his outfit and sighs. “Probably shouldn’t with this get-up.”

“True. I can get you a water if you want.”

“Hey, you’re the debutante,” he says. “Shouldn’t I be waiting on you?”

She smiles. “I like the sound of that.”

“One water, coming right up.”

“They’re in the fridge,” she calls after him. She smiles to herself as she sits back down on the couch, and Lorelai eyes her curiously. When Rory catches this, she glares. “Shut up.”

“Hey, I’m not saying anything.”

“No, but your eyes are.”

“Damnit. They always give me away. Nice going, boys.”

Rory smiles and shakes her head in response.

Jess walks towards the kitchen, remembering where it is from when he brought Rory home from the party. Christopher is sitting at the kitchen table on the phone, only giving Jess a quick glance when he enters the room. They haven’t really interacted much this week, but he gets a pretty clear message that Christopher does not approve of him - which, of course, is fine by Jess. He’s never been one to seek approval, anyway. Besides, he isn’t even with Rory. It doesn’t matter. 

“Didn’t you talk to Harrison about that?” Pause. “No, no,  _ Harrison.  _ Robert Harrison.”

Jess opens the fridge. He eyes the beer, but quickly remembers Christopher behind him and the suit, so he grabs a couple water bottles and closes the fridge. 

“Alright. You too. Bye.” Christopher hangs up, setting his cellphone down on the table. It’s quiet for a moment before he turns his head right as Jess is closing the fridge. “Jess.”

“Sir,” Jess says with a nod, although the both of them can detect the underlying layer of sarcasm. 

“Why don’t we talk for a moment. You and me.”

“I’m good.”

“That wasn’t a question,” Christopher says firmly before Jess can walk out of the room. Silently cursing, Jess takes a seat at the kitchen table for the second time, right across from Rory’s dad. “Look, I don’t know what Lorelai told you, but-”

“She’s told me enough. Apparently you played the hero a few weeks ago, brought Rory back from a party.”

_ Hero? As if.  _ “Huh.”

Christopher seems to observe him for a moment - as if he has Terminator vision or something. “I consider myself a good judge of character most of the time,” he begins, “and I think I can read people pretty well. So when my daughter has a new boyfriend-”   
“I’m not her boyfriend,” Jess says flatly.

“I don’t trust you,” Christopher says. “And I don’t like you. Not for Rory, not in general.”

“As far as I’m concerned, you don’t have to,” Jess replies flatly. “You’re only around, what, once a year?”

Christopher’s eyes narrow. “Watch it, kid. I’m Rory’s father-”

“Barely,” Jess snorts, unable to help himself. 

“Hey, you know nothing about me or my family, okay?”

“Trust me, I know an absentee dad when I see one,” Jess mutters, getting up from his chair. “This whole conversation is worthless. I’m just a friend.”

“I won’t help you with that collar,” Christopher calls after him as Jess walks off.

“Wasn’t going to ask.”

Jess comes back into the family room and hands Rory her water. She thanks him, but frowns a bit in the direction of the kitchen.

“Were you two talking back there?”

“I guess.”   
“What were you talking about?”

Jess glances in the same direction. “Oh, nothing. He just told me he didn’t like me.”

Rory’s eyes widen. “I’m sorry, he said  _ what?” _

“Get mad at me instead,” Jess advises, taking a seat on the other end of the sofa, leaving just enough distance between them. “I called him an absentee father in response, so.”

Related or perhaps not, Lorelai chokes on her sip of water. As her mom coughs, Rory’s face is unreadable, but Jess doesn’t see any anger as she stays silent.

Lorelai coughs a couple more times before stopping. “Okay,” she says, swallowing. “So, no one’s going to ask if I’m okay?”

Rory shrugs. “You seemed to be managing just fine.”   
“Geez, at least I know who  _ won’t  _ save me when I’m actually dying.”

Rory shakes her head in amusement and goes back to her book.

**

They continue to get ready for the ball. Christopher returns from the kitchen, Lorelai adds some finishing touches to Rory’s hair, and Jess reads the book he brought, perfectly content to stay out of everyone’s hair.

“Hey, Rory, remember when we watched  _ Sound of Music  _ last week?” Lorelai asks, putting on her coat. 

“Yeah, why?”

Lorelai straightens in an effort to appear serious. “Well, I had Sixteen Going on Seventeen stuck in my head, as one might, so I started to think about the lyrics.”

“Right.”

“And I realized - that song is, like, the most misogynistic thing I’ve ever heard!”

“I don’t know about that,” Christopher interjects, but Lorelai waves him off.

“Think about it - ‘ Your life, little girl, is an empty page that men will want to write on-’ what the hell is that?”

Rory makes a face. “Oh, yeah, you’re right. That sucks. It’s catchy.”

“‘Totally unprepared are you to face a world of men-’”

“Okay, Lor-”

“‘Timid and shy and scared are you of things beyond your ken-’ I mean, who wrote this piece of junk?”

“Richard Rodgers?” Rory suggests.

Lorelai scrunches up her face. “Well, I hate him. I mean, ‘you need someone older and wiser telling you what to do-’ it’s disgusting.”

Rory zips up her coat. “And why are you bringing this up?”

“Well, since you’re now a young lady of noble breeding,” Lorelai explains in a haughty voice, “I figured we needed to rebrand, starting, of course, with a theme song-”

“Oh, my god!”

“C’mon, sing it with me now-”

“Mom!”

Lorelai starts singing as the four of them walk out the door. Jess shakes his head in amusement and closes the door behind them. 

**

Once they arrive, Rory is directed towards a room where she can get ready. She’s told, of course, that since she wasn’t early she can’t get a mirror with lights, but somehow, Rory thinks that she’ll survive.

She takes a seat next to a blonde girl with short hair who is doing the finishing touches on her makeup. Having already changed into her dress, Rory just sits down and takes out her book, but when she feels a tap on her shoulder, she closes it and looks up.

“I’m Emma,” the girl explains with a smile. “And you are?”

“Rory. Rory Gilmore.”

“Well, it’s nice to meet you, Rory Gilmore.”

Rory smiles back. “You, too.”

“So, is this your first?” Emma asks.

“My first?”

“Your first coming out,” the girl explains. “You’ve got it written all over your face. Bambi eyes, that sort of thing.”   
Rory frowns. “Oh. Um, thanks?”

“This is my third,” Emma continues, unbothered. “They say one out of three girls marry their escorts, so I’m really hoping this one sticks. The last two? Absolute bores.”

“Oh,” Rory says, knowing it sounds lame, but even she is struggling to keep up with this girl. 

“So, what about you?”

“What about me?”

“Your escort,” Emma says, as if it should be obvious. “Is he the one?”

“He’s just a friend.”

Emma laughs. “Yeah, I’m sure.”

“No, really. Just a friend.”

The blonde girl shakes her head. “You won’t be for long. Just friends, I mean. Trust me, I know these things.”

Rory fidgets uncomfortably. She can’t stop thinking about  _ I lost you  _ and  _ it’s whatever you want it to be  _ and everything else he has and hasn’t said. She wants to think that maybe, just maybe, he likes her, but then she remembers that that’s what she thought the last time. She can’t afford to mess up again. 

_ I should’ve said something. What I did...it wasn’t okay. You just...you caught me off guard, and all I could think was that- _

“Rory? Hello?”

Rory blinks, realizing she’d zoned out. “Sorry. What were you saying?”

“I was asking about your escort. Who is he? What’s his name?”

Rory bites back a smile - god, this girl is persistent. “His name is Jess.”

“Huh. Weird name for a boy.”

Rory shrugs. “I think it fits him.”

“That’s what counts,” Emma says matter-of-factly. “Well, I’m curious to see you two together. I’m telling you, if he’s agreeing to be your escort, he wants to be with you. Or sleep with you,” she adds as an afterthought, making a face at what Rory assumes is a less than favorable memory. “But hopefully the first one.”   
“Well...we’ll see,” Rory breathes, offering a smile.

Emma nods wisely. “Yes, we will.”

**

“Lorelai Leigh Gilmore, daughter of Christopher Hayden and Lorelai Gilmore.”

As Christopher escorts her down the staircase, Rory can’t help but smile. There’s an odd feeling in her chest, but she thinks it’s a good one. Her father is by her side, and that’s all she’s wanted for a long time.

But then, there’s Jess. Christopher hands her off to him, looking less than pleased to do so, but then she’s arm in arm with Jess and it hits her. There’s something else,  _ someone  _ else, that she thinks she wants even more.

**

The music starts up, but there isn't a fan in her hands this time. She and Jess stand as Miss Patty instructed them to, and they begin to move to the music. She’d worried that maybe the failed dance lesson had been a sign, that they wouldn’t make it through the ball without embarrassing themselves, but she finds herself pleasantly surprised as Jess keeps them on time and on their feet.

“So,” she says after a moment.

“So.”

She looks up at him. “Thank you, Jess. For...everything. It means a lot.”

He gives her his half-smile, something twinkling in his eyes. “What kind of friend would I be if I didn’t escort you to the Daughters of the Daughters of the American Revolution debutante ball?”

“God, the name itself gives me a headache.”

He laughs. “It’s a mouthful.”

“That it is.”

“But seriously,” he says, “there’s no need to thank me. I’d do a lot of things for you, you know.”

She blushes and looks down. “Jess.”

“Besides, I think you look very elegant here. Maybe you should give up on the journalism thing, become a DAR lady.”

She scrunches up her face in disgust. “You really think I could be a DAR lady?”

“Maybe for a month.”

“I’d say two. I’ve got stamina.”

He laughs again. “Okay. Two.”

They fall silent for a moment, but it’s not a bad silence at all. Dancing with Jess is proving to be quite enjoyable, and the quiet doesn’t feel uncomfortable at all.

_ I've been waiting a long, long time / Don't let love pass me by… _

“I want you to know that I wasn’t just saying that,” she says suddenly. “The thank you. I meant it.” She looks him in the eyes, trying to express what she can’t bring herself to say. “I meant it about a lot of things.”

“Well, what are friends for?”

The second reference to being  _ friends  _ is a bit disheartening, but then he squeezes her waist a bit and smiles playfully, and it slips her mind.

“You know, your grandma was talking about how you should do this more often.”

“What? No!”

“What, you don’t like this?”

“No, I do!”

He raises an eyebrow and smiles.

Her face grows warm. “I mean -  _ this,  _ I mean, the ball - not that, not that dancing with you is bad, I-”

“Breathe,” he reminds her, and she can’t help but laugh a little. 

“I wouldn’t want to do this whole thing a second time,” she explains.

He shrugs. “Why not? I’m telling you, being a Hartford high society Donna Reed-” She laughs and pinches his shoulder. “That’s your destiny.”

“Whose side are you on?” She asks jokingly.

He locks eyes with her, and her stomach drops while her heart skips a beat. He leans in to murmur in her ear, “Yours always, darling.”

She blushes as he pulls away. She stares at him in confusion before it hits her and she smiles. “North by Northwest.”

“And we have a winner!”

She laughs, and then they’re quiet. She’s overly aware of their interlocked hands and his hand on her waist and a million other things that fade away when their gazes meet once more.

She thinks she feels something shift that night, but she can’t be sure. All she knows is that she still wants this, wants  _ him,  _ and his words from earlier in the week...maybe this time, they can get it right.

_ I've been a good guy all of my life / Don't, don't let love pass me by / Don't let love pass me by... _


	26. The Castaways

**Summary for the Chapter:**

> Jess and Rory re-examine their history - and their future.

Rory glances over at Jess, his nose buried in a book. She looks back down at her watch, watching the seconds tick away.  _ Three, two, one- _

“Okay!” She exclaims as her timer goes off. “Break over. Time to get back to work.”

“One sec,” Jess says, not looking up from his book. 

Rory rolls her eyes. “No, not  _ one sec. Now.”  _ She reaches over to try to take the book out of his hands, but his reflexes are quick. He hops up and holds her at arms length as he keeps his eyes on the page. Rory huffs and gives in, glaring at him until he snaps the book shut.

“Okay. Ready now.”

She grumbles under her breath as they sit back down at the table. Jess grabs one of the legal pads and scans over what they have written so far, brow furrowed in concentration. “Do we have enough?” She asks hopefully. It’s getting late, and she and her mom have plans to marathon  _ Cop Rock.  _

“I think we’re missing a little on the consequences of the crisis,” he says thoughtfully. “We talk a lot about how Carter handled it, but we don’t connect it enough to the election of 1980. Or diplomatic relations following all of it.”

“So, what now?”

“Snack break?” Jess offers, setting down the pad.

She gives him a look. “Jess.”

“What? I’m hungry.”

“You just had a danish,” Rory reminds him, gesturing towards the counter behind them. “And I don’t think Luke would appreciate you digging through his kitchen.”

“I can reimburse him.”

“Do you want an ‘A’ or not?”

“I have a reputation to uphold, Gilmore. An ‘A’ would absolutely ruin it.”

She hits him in the arm.

Jess swats at her a little too late. “Okay, jeez, not a fan of the late night comedy. Got it.”

“We don’t have enough information, as you informed me two minutes ago,” she says sternly. “We need to do more research.”

Jess wordlessly gestures towards the small stacks of books on the table in front of them. 

Rory shakes her head. “We read all of them already. We need new material.”

“Your computer is literally right there.”

“Mrs. Ness said books only,” Rory counters. 

“Okay, so, we go to the Stars Hollow Library.”

“It’s closed for repairs,” Rory reminds him not all that gently. “Besides, do you really think they’d have what we’re looking for?”

“We can break in and find out,” Jess offers.

She gapes at him. “Jess!”

“Fine, fine,” he relents. “You’re no fun, you know,” he says, his eyes sparkling with something a little dangerous.

She swallows and glances away. “We can just use the Chilton library.”

“Come on, Gilmore, really? I know you love school and all, but it’s almost ni-”

“Tomorrow,” she interrupts forcefully. “Obviously. Chilton is absolutely not open at this time of night - and you knew that,” she adds when she sees his mischievous smile. “You suck.”

“Oh, I’m not so sure about that. I think I’m very funny.”

“I hate you,” Rory grumbles, starting to put some of the books in her bag. 

Jess just smiles to himself, leaning back in his chair. 

“So, we’ll meet up tomorrow after school?” She asks, zipping up her backpack and standing up. 

“Okay.”

“See you later, Jess,” she manages with a smile. He nods at her in response before she turns and leaves the diner, the door chiming behind her.

Ever since the debutante ball, they’ve been in some sort of limbo - friendship-romance purgatory, if you will. She’s a little afraid of ruining it all again, but he seems to be unbothered, so she tries to be, too.  _ Just go with the flow. Whatever’s meant to happen will just happen. _

The thing is, though, nothing seems to be changing. They’re on the precipice of something that could be wonderful, but if she falters, the fall is a long way down. 

It’s been two weeks of something reminiscent of what they used to have, but so much more is unspoken between them.  _ Yours always, darling.  _ So why hasn’t anything changed?

**

The bell rings. Rory waits outside the library doors, watching her classmates pass by as she waits. Some several minutes later, one of them is finally Jess. 

“Took you long enough.”

He holds his hands up in mock surrender. “Sorry,  _ mom.” _

“Gross. Don’t do that.”

Rory pushes past the large set of doors into the library and Jess follows. Once they’ve entered, Rory glances down at her legal pad. “I took the liberty of looking up some possible books they might have-”

“Wouldn’t it be easier to just ask the librarian?” Jess asks, glancing over towards the main desk.

“I did research,” Rory protests.

Jess shakes his head. “Fine. Where do we start?”

“Well, if it’s 900-999 for history and geography, and the first author’s name starts with K, then-”

“Don’t tell me you memorized the Dewey Decimal System,” Jess chortles. Rory looks at him crossly.

“For the record, I’ve had it memorized since I was seven,” she says defensively, which just amuses Jess more. “Anyway, we should start looking. The school closes at six tonight and the storm is only going to get worse.”

As if to punctuate her point, a loud clap of thunder shakes the building. 

She starts making her way towards the 900s when she notices that Jess is going in the opposite direction. “Where are you going?”

Jess shrugs. “Looking for the books we need.”

“They’re the other way.”

He just waves and turns back around. Rory rolls her eyes and walks in the  _ correct  _ direction. She navigates the aisles, finally stumbling across the section that they were looking for. Jess, of course, is nowhere near her, so she makes a mental note of the aisle and marches back to go get him. She finds him in the fiction section by the Hemingways, so she ignores his protests and grabs his wrist, dragging him over to the aisle they needed to be in in the first place. 

“You’re gonna wrinkle the shirt.”

“Can it!”

She starts pulling books off the shelves and handing them to him. “We’ve got three hours to get as much information as we can,” she instructs, adding a fifth and final book to the stack. “I have the notepads so we can take notes.”

Jess grimaces under the weight of the books. “You really think we can finish in time?”

Rory grins and sits cross legged against the wall. “What are we if not champion readers?”

“Yes, but you’re  _ slow.” _

“Take that back!”

He laughs under his breath and takes a seat next to her. His knee brushes up against hers ever so slightly, and she hates how her whole body freezes.

She doesn’t realize he’s taken a book to read until he nudges her in the side. “Earth to Rory, it’s time to get started.”

She laughs shakily. “Hand me a book, will you?”

**

When you’re an avid reader like Rory and Jess, it’s easy to lose track of time. God knows Rory’s done it multiple times, including the time her mom lost her in a K-Mart because she’d found a copy of  _ Madeline  _ in the discount book bins and found a nook to read in. But books on the Iranian Hostage Crisis aren’t necessarily page turners when you already know your AP United States history, so she’d assumed they’d be fine.

Apparently not.

They’ve been reading for a while now, making their way through the five books she picked out. Jess is admittedly reading a lot faster than her, but in Rory’s defense, she’s making a lot more notes than he is. She’d scold him for that, but he  _ does  _ remember practically everything he reads, so she lets this one slide.

She’s halfway through the fifth chapter of  _ America Held Hostage: The Iran Hostage Crisis and the Iran-contra Affair  _ when the room goes dark, startling them both into reality.

“What just happened?” Rory hears herself ask.

She can see faintly Jess’ figure move as he checks his watch.  _ “Shit.” _

“What is it?” She asks, but she has a feeling she already knows. “What time is it?”

Jess looks up. “6pm on the dot.”

“We’ve been reading for  _ three hours?”  _ Rory asks in shock, shakily standing up. 

“Guess so.”

“Oh god,” Rory mumbles, suddenly feeling a little sick. She starts making her way towards the big library doors. Jess follows her at a similarly frantic pace. She pushes the doors and they open, but Jess isn’t as relieved as she is.

“Oh, thank god.”

“The door to the school is still going to be locked,” he points out. She knows he’s probably right, but part of her is still hoping that there’s a way out.

“Come on,” she says, tugging at his wrist. “Maybe the janitor hasn’t left yet.”

Jess nods solemnly. Her heart is beating out of her chest with anxiety and she doesn’t understand how collected he seems, how the only sign of worry is his furrowed brow.

They hurry down the hallway towards the main entrance to the school. When Rory tries to force it open, it remains shut. She can see the janitor getting in his car so she bangs on the window. Jess does as well, the both of them yelling for help, but to no avail. The janitor drives away, leaving the two of them behind. Rory presses her forehead against the window in defeat, watching the sheets of rain come down. 

Jess curses under his breath, but he doesn’t appear nearly as panicked as Rory feels. “What are we going to do?” She asks in a small voice.

“I don’t know,” Jess admits. “Call your mom?”

Rory takes a shaky breath. “Okay. I’ll call my mom.”

They trudge back to the library in defeat. Jess holds the door for her as she takes out her phone and dials her mom’s number. It rings a couple times before Lorelai picks up.

_ “Lorelai Gilmore, Nuisance of the Year speaking.” _

“Mom?” Rory says, feeling a surge of anxiety for no reason in particular. Jess finds the light switch and turns the lights back on, the room suddenly basked in a warm glow. 

_ “Hey, hon. What’s going on? I’m getting our smorgasbord of food set up for our marathon tonight - I think Al is planning to kill me for all the takeout boxes I used up.” _ _   
_ “Mom, I don’t, um, I don’t think I’ll make it back in time for the marathon.”

_ “No worries, babe, I can wait. It makes sense - with this rain, I bet your bus is held up.” _

“Well...not exactly.”

Pause.  _ “Then...what is it? Kidnappers? Sneeze twice if you’re being held against your will.” _

Rory squeezes her eyes shut and takes a breath. “Well, Jess and I were doing research for our paper in the Chilton library - we would’ve just gone to the Stars Hollow Library, but that’s closed for repairs, and I didn’t want to break in - but we were reading, in the library, and I guess we lost track of time or something, because suddenly the lights shut off and now we’re locked in the school and we can’t get out.”

There’s another beat of silence on the other end while Lorelai processes everything.  _ “Let me get this straight. You’re locked in your fancy-schmancy school overnight because you lost track of time while _ reading?”

“Yeah.”

To Rory’s surprise, her mom starts to laugh.  _ “Oh, my god. This is the most ‘Rory’ thing you’ve ever done.” _

“Mom!”

_ “Right, right, sorry. And there’s no unlocked exit or anything?” _

“Nope.”

_ “I can come to get you, but - no, I don’t have a key or anything and I’m not risking breaking in...maybe try calling the police?” _

Rory glances out of one of the windows. “It’s storming really bad. Would anyone actually be able to get here safely?”

_ “I think we can spare a few of Hartford’s finest. What is it that the kids say? Fuck the police?” _

“Mom, I’m being serious.”

Lorelai sighs.  _ “Hon, I hate to say it, but...you might just have to stay there overnight. You can try calling the cops, but if they can’t come…” _

Rory groans. 

_ “I know, I know. But try making the best of a bad situation.” _

“How do I do that?”

_ “You’ve been wanting to make things better with Jess, right?” _

Rory nods, then realizes that of course, her mom can’t see her. “Yeah.”

_ “Well, if you’re stuck with him overnight, this might be the perfect chance to make up and sort everything out. Although, don’t make up  _ too  _ much, if you know what I mean.” _

“Oh, my god!”

_ “Do you feel safe there? I know it’s probably creepy, what with all the ghosts and whatnot, but are you going to be okay?” _

Rory glances over at Jess. He’s leaning up against one of the ables and drumming his fingers against the table. He notices her staring and she looks away quickly. “Yeah. I do.”

_ “Keep checking in with me, okay?”  _ Lorelai asks.  _ “Even if it’s just a page to let me know you’re alive.” _

“Okay.” Rory swallows, suddenly feeling like she wants to cry. “I’m sorry, mom. I didn’t mean for this to happen. It was a mistake, and it’ll never happen again, I promise. I-”

_ “Breathe. Trust me, I’ve done worse. When you’re eighteen I can elaborate.” _

Rory lets out a shaky laugh. “Okay.”

_ “It’s gonna be fine.” _

“Thank you.” Rory looks at Jess again. “Mom...can you tell Luke?”

_ “I guess, but I’m not responsible for his reaction, got it?” _

“I think you could take him down if need be.”

_ “Probably. I’m wily.” _

Despite the situation, Rory manages a smile. “I’ll check in with you later.”

_ "Okay.” _

“Goodnight, I guess.”

_ “Stay safe.” _

Rory hangs up. She walks over to the table Jess is leaning against and collapses into one of the chairs. She feels deflated and defeated and  _ exhausted,  _ but she knows she’s got a long night ahead of her. She knows her mom told her this could be a chance to change things with Jess, but this limbo of theirs is quite safe, she’s realizing. She thought she wanted things to change, but now that the chance is in front of her - why is she so scared?

Jess nudges her foot with his. “It’s gonna be fine,” he says with an apologetic look on his face. “I mean, there’s gotta be an upside, right? Like-”

“Stop it, Jess,” she snaps. “I don’t want to hear it.”   
He frowns. Thrown off, he looks away, his grip on the table slightly tighter.

“Besides,” Rory continues coldly, “there is no upside. Not if I’m stuck here with you.”

The silence that follows her response is unnerving, and Rory starts to feel guilty. She can’t take it back, though, and maybe that’s for the best - it was admittedly so much easier when they weren’t on good terms. Even if it hurt, it hurt less than knowing how she felt about him and that he didn’t feel the same way. 

She allows herself to look at Jess, and when she does, she’s surprised to see that instead of looking angry or upset, a deep-seated  _ worry  _ is etched in his face. “Why are you acting like this?” He asks, but it isn’t harsh or defensive at all.

“Acting like what?” 

“You know what I mean. What just happened?”

She gets up from her chair and stops a few strides away from him, still not looking at him. “I tried to pretend that we could go back to how it was...before, but we can’t.”

“Rory…”

She takes a breath. “I wanted everything to be normal again, so I tried to forget what happened and forgive you, but…”

“You can’t,” he finishes for her dryly.

She finally steels herself and turns around to face him. His expression is unreadable as he watches her. “I’m sorry, Jess. I want you in my life, I do, but isn’t there a point where we just need to accept that we don’t work? That we’re better off-”

“Don’t say it.”

“Jess,” she pleads. “People drift apart. You can’t hold onto people forever.”

“People drift apart.  _ We  _ don’t.”

She can tell that he’s getting a little worked up, and they’re surely going down the same path as always, but she can’t stop herself. He needs to understand her side, to fully get why she can’t do this.

“Don’t you get it?” She says, voice nearly a whisper. “I can’t even  _ look _ at you without being reminded of the ski lodge and our fights and how much it hurt to lose you. There’s too much history here, Jess, too much for us to ever be able to rebuild our friendship.”

He moves as if to speak, but he stops himself. She waits, but he stays silent.

“I know you apologized,” Rory continues, “and I know that things have been a little different lately. But I think I was kidding myself. Whatever we do, I still told you how...how I felt. And you didn’t say  _ anything.  _ I can’t forget that.”

“But then you took it back,” he says in a low voice. “You never liked me, right? You were...confused.”

She stares at him for a moment, temporarily at a loss for words. “That doesn’t matter,” she tries to argue, but he won’t have it.

“It does,” Jess insists. “If you don’t feel that way, then there shouldn’t be anything to be angry about.”

“But-”

“And why don’t I get to be angry? Why don’t I get to be upset that you told me you liked me while you had a boyfriend already? You put me in an impossible situation.”

“It wasn’t impossible.”

“What should I have said, Rory?” He demands. She remains quiet, and he nods. “That’s what I thought.”

“Jess…”

“And then you just dropped me, like I meant nothing to you. You were just...done, immediately, without ever giving me a chance to explain myself.”   
“You did! After that party, you apologized. You explained your side to it.”

“Then why has nothing changed?”

“I can’t trust you, Jess!” Rory exclaims. I thought you liked me, but then you hurt me, and now - I don’t even know. You’ve been so  _ vague _ lately, saying all these things-”

“What do you mean?”

She scoffs. “Saying that you...you lost me, or that you’re fine waiting? What does that even mean? It’s the same thing that happened before, with you making me think that you…” She trails off.

“That I what?” Jess asks flatly.

“You know what I mean.”

“No, actually, I don’t,” he says. He straightens up and walks closer to her. “What am I making you think?”

“It’s the same thing as before,” she repeats, “when you kept leaning in close and taking my hand and making me think that you felt something for me, and in turn making me feel something for you, and then it just blew up in my face when I tried to act on it. And everything that you’ve been saying to me lately, what happened at the ball…”

His jaw is tight as he listens to her, but he doesn’t say a word.

“And then you got together with Zoey right after it all fell apart between us.”

“And you had a boyfriend,” he nearly growls. “People in glass houses, right?”

They fall into a tense silence. 

She sighs, running a hand through her hair. “God, it’s always just the same fight every time, isn’t it?”

“Seems like it.”

“We just shouldn’t talk about this right now,” she says quietly. “It’s not a good idea.”

Jess hesitates for a moment. “So what’s next? You, me...where do we go from here?’

She forces herself to look fully at him. There’s something unreadable in his eyes, but the look in them fills her with guilt when she speaks again. “There is no you and me, Jess. Not anymore.”

There’s a flash of pain and anger in his eyes before he breaks the gaze. They’re stuck in a horrible silence for a moment until he clears his throat. “I’m just gonna…” He mumbles something under his breath about exploring before he walks past her and out the library doors.

She watches him leave before forcing herself to look away. She doesn’t follow him.

Figuring she should instead make the best of a bad situation, she returns to the aisle they were sitting in before this all started. She does whatever Rory Gilmore would do when stuck in a library overnight - she picks up a book and reads.

**

She’s unsure how long she’s been reading - Jess is the only one of them wearing a watch today - when she hears a noise from the other end of the library. Suddenly convinced that there’s a robber or possibly a murderer, she grabs one of the thicker books they were reading and creeps along the aisles. She turns the corner and nearly jumps out of her skin when she runs into Jess.

“What are you doing?” He laughs, looking at the book in her hands.

She turns red. “I thought I heard someone.”

“Yeah. Me.”

“Well, excuse me from trying to defend myself from a potential robber,” she says haughtily, but she’s starting to smile.

“That’s adorable,” he says, “trying to attack a robber with an Encyclopedia. Very creative.”   
She scrunches up her face at him. “Well, we can’t all be master strategists.”

“I guess not.” Pause. “So, I’ve been thinking.”

“About what?” 

For a second, she thinks he’s going to bring up their argument from before, but then he smiles. “We need to make the most out of this situation.”

“And what would that entail?”

He grins mischievously. “Well, you’ll just have to follow me to find out.”

“What, Jess-” She scrambles to put her thoughts together, but he’s already heading back towards the library doors. She hurries after him and down the hall.

“Where are we going?”

Jess shakes his head. “Jeez, you’re impatient. You’ll find out when we get there. Now hush.”

“But-”

“Hush.”

She gives in and shuts up, following him down the hall and up the stairwell. She starts to wonder if maybe she should be worried when he stops in front of the door to the cafeteria. 

“You’re not going to be able to get in there.”

He grins and raises an eyebrow before pushing the door open.

She gives him a look. “You got lucky.”

“No, I got here fifteen minutes ago and picked the lock.” He holds the door and gestures for her to go in. “Ladies first.”

She rolls her eyes, but she steps inside.

“Are you sure we should be in here?” She whispers as he leads her through the cafeteria. 

He eyes her amusedly. “Why are you whispering?”

“I don’t know. It’s dark and eerie.”

“We’re literally the only two people in the building, Gilmore.”

“Oh, shut up and keep walking, Mariano.”

He laughs. “To answer your question...I don’t know about  _ should,  _ but...we need to eat, don’t we?”

She frowns. “And where are you planning on getting this food?”

“Where do you think?”

“Oh, we are  _ not  _ stealing from the kitchen!” Rory objects, following as he pushes open the door that leads to the kitchen. “This food belongs to the  _ school, _ and we can’t just take it paying-”

“Relax,” Jess interrupts. He reaches into his pocket and pulls out a twenty. “I’ve got it covered.”

“Where did you get that?” She demands.

He opens a fridge door. “Mugged Babette.”

“Jess.”

“I work at the diner, remember?” He reminds her dryly, taking out a couple bagels from the fridge and closing the door. “Bagels okay?”

“I guess. But-” 

“I am putting the money in the register, okay?” Jess says, making a show of opening the register and putting the twenty in. “It’s in. Are we done here?”

She can hear her mom’s  _ dirty!  _ in the back of her mind, and she holds back a smile. “Fine. Get butter, though. Or cream cheese, if they have it.”

“Order up!”

**

Rory starts eating her bagel as they walk back down the dark hallways. It’s so surreal to be there at night, with all the classrooms locked and not a soul besides the two of them. 

“Let’s make another stop,” Jess says all of a sudden, his voice echoing in the empty hallway.

She frowns in confusion. “Where could we possibly make a stop besides the bathroom?”

“Teacher’s lounge,” he says, as if it should be obvious. 

“Now  _ that  _ is going to be locked.”

“Ah, but you forget, I’m a master at breaking and entering.”

“My mistake. But how are you-”

“Watch and learn.” They stop in front of the teacher’s lounge. Jess reaches into his pocket and pulls out a pen cap. She watches with mixed bewilderment and awe as he crouches down and starts picking the lock with the cap. The way he bites his lip in concentration makes her blush. 

Finally, he straightens up and tries the handle, and sure enough, the door opens. He looks back at her, looking quite pleased with himself. 

“I can’t believe I’m aiding and abetting you with a  _ crime,”  _ she remarks.

He shakes his head, amused. “I’ll make sure not to mention my accomplice when I get arrested.”   
He closes the door behind him and she turns on the lights. “So, why are we stopping in here again?” She asks, looking around at the room. Admittedly, she’s a little excited by the idea of being in the teachers lounge, but she keeps it to herself, knowing Jess would have a field day with that.

Jess gestures towards the counter. She looks in that direction and then squeals in excitement.

“There’s a coffee machine in here!”

Jess dips his head in a nod. “Thought that would make you happy.”

Rory grins and hurries over to the coffee maker. “You know me so well,” she gushes, immediately getting started.

He smiles to himself. “I do.”

Once she’s satisfied with the quality of the coffee, she pours two cups and settles down at the table with him. “I wasn’t sure how much sugar you wanted, so I only put in one-”

“One is fine,” he reassures her. She smiles in response. 

As they eat, Jess tells her stories about living with Tristan, making a point of telling humorous ones just to get Rory to laugh. In return, she tells him stories from growing up with her mother, a warm feeling settling in her stomach when she makes him laugh. 

Their fight from before is temporarily forgotten, and for that, Rory is grateful. She regrets the things she said, and she hopes he can tell, but she won’t risk bringing it up again. They’ve achieved equilibrium again, and she’s not going to upset the balance all over again. When he’d walked out that door, she’d felt a moment of panic, like that if he left, she’d lose him forever. She doesn’t know if it’s better to have him in her life or have him leave. Both would hurt, but when they’re sitting at the table and talking like two old friends, she’s starting to think the pain that comes with being friends might be worth it. 

**

After they finish their coffee and bagels, they continue to explore more of the school. He asks her if there’s any classroom she wants to get into, and while she’s hesitant at first, his mischievous grin makes her smile and give in.

“Math class,” she decides. “Maybe I can get a head start on homework!”

He reaches into his pocket for the pen cap and grins. “As you wish.”

**

“Knight to C4.”

Rory pouts as Jess captures her remaining bishop. “I hate that you’re so good at this.”

“Hey, you’re not too bad at this yourself.”

“I have, like, four pieces left on the board,” she points out. “Aha! Got your last rook.”

He shakes his head in amusement at her triumphant grin before moving his queen forward. 

They play in silence for a little while until they both only have three pieces left on the board. Jess still has his queen, but Rory is very proud of herself when she manages to capture it with her knight.

“Checkmate!”

He stares at the board for a moment to confirm before nodding in approval. “Well, I’ll be damned, Gilmore,” he drawls. 

She grins and extends her hand for him to shake. “Good game, Mariano.”

“Good game.”

She drops her hand and they fall back into silence. She’s starting to wish she had a change of clothes, but she’s at least taken off the snap tie from around her collar and kicked her shoes off a couple hours back. Jess’ tie is off as well, left in the aisle they had been sitting in before all of this began. 

She’s staring at one of the shelves, reading the titles when he speaks up again. “Do you like it here?”

She turns her head back to face him, confused. “You mean right now, at night?”

“No, just…” He swallows, suddenly looking very young in the moonlight. “Do you like it at Chilton? Are you happy here?”

Rory hesitates. “Yeah,” she says after a moment, smiling a little. “I do. I mean, it’s hard, definitely, and it took me a little while to adjust, but...it’s helping me get somewhere, you know?” He nods. “It’s helping me get to where I want to be. Going here is a step towards Harvard, and then becoming…”

“Christiane Amanpour,” he offers. 

“Yeah. I wasn’t going to get into Harvard, not going to Stars Hollow High. So I’m really, really grateful that I get to go here.” She bites her lip, suddenly feeling very self conscious. “And, well, you know, Chilton...well, it brought me Paris, and…” She takes a breath. “Well, it brought me you.”

He looks surprised, but she thinks she sees a hint of a smile behind his guard.

“So, what about you?” Rory asks quickly, feeling awkward. “Do you like it here?”

Jess sighs. “Well, it’s school. I’ve never enjoyed school, never really understood the particular need for it, but...I’ve been to ones that are worse.”

“Is that it? Just the lesser of all the evils?”

“Sort of, I guess, but not exactly.” He fiddles with one of the pawns, not quite looking at her. “The workload here, it’s more, which I don’t like. But there’s at least some adults here that I can...that I can trust. And I’ve never had that before.”

“Like Mr. Medina?”

He takes a breath. “Yeah. I guess I’ve just never had a teacher  _ care  _ the way he does, you know? I never would’ve thought a teacher would be willing to take me in when I needed it.” He laughs under his breath. “But he just kept surprising me.”

“He’s one of the good ones,” Rory says softly.

Jess glances up and meets her eyes. “There’s a lot more of those here than I would’ve thought.”

When the intended meaning of his words sink in, Rory blushes, but she doesn’t look away. After a moment, he clears his throat. “Well, we should probably-”

“Jess?”

He stops collecting the game pieces to look at her. “Yeah?”

“Why don’t you like school?” She asks after a moment. “Like - I’m not saying that you  _ should,  _ but you’re not out of place at Chilton. You’re really smart and you’ve read more than anyone, even me, and you remember everything...you could be acing all of your classes if you tried. Why don’t you?”

He thinks over her question for a moment, rolling one of the pawns between his fingers. “It’s not that I’m opposed to  _ learning _ or anything,” he says slowly. “That’s part of reading, isn’t it? Learning about people and places you would never have known otherwise?” 

“So why don’t you like learning at school?”

“We don’t get to choose what we learn,” he replies. “I mean, I could care less about the pythagorean theorem or quadratic equations. I’m never gonna need those, but we’re forced to learn about them anyway.”

She nods, thinking she gets it - she’s not a huge fan of math, either. “But things like that are to help with problem solving skills.”

“I know, but even that learning doesn’t seem as important to the teachers as our grades do. The grades define us, and it takes away from the learning and just makes it seem...like it’s not worth it.” 

“So…” she swallows. “I get what you mean, but...if you hate it that much, why are you all of a sudden trying now? You’re putting effort into your assignments, publishing your amazing stories in the lit mag...but why now, if it doesn’t matter?”

“Ah, but that’s where you’re wrong,” he says, pointing the pawn he’s holding at her. “Maybe I hate it, and think it’s more or less pointless in the grand scheme of things, but it matters.”

“What made it matter, though?” She questions. “When we first met, you couldn’t care less.”

Jess meets her gaze, and something in his eyes makes her heart twinge. “I think you know.”

“Oh.” She takes a deep, shuddering breath. “Oh.”

“So, we should probably bring this back to the classroom, then,” he says, gesturing towards the chess set.

Rory nods. “Yep. Yep, we should.”

“And then we could watch a movie.”

She looks up from gathering the pieces and frowns. “What?”

Jess rolls up the board. “There’s a projector in Mr. Remmy’s room,” he explains, “from when we had to watch that documentary on Shakespeare, remember?”

“Oh, yeah.” She puts her pieces back in their bag. “That could be fun.”

“So?”

She looks up and sees his expectant expression. The corners of her mouth turn up. “Let’s do it.”

**

Jess unlocks the classroom door (seriously, how does he know how to do that?) and they slip inside to look at the films. Rory already grabbed some chips from the vending machine, which she sets down on one of the desks to be able to look with him.

“Okay, so we’ve got a driver’s ed film, something about the birds and the bees, and-” He stops short.

She frowns. “What is it?”

“Never mind,” he says quickly. “Okay, so, the dangers of the road or a million and one ways to scare teens out of sex?”

“Why won’t you tell me what that one is?”

“Rory-”

She moves quickly and snatches the third canister from it. As she reads the title, a broad grin spreads across her face as he watches, looking pained. “Oh, yes, we are  _ definitely  _ watching this.”

“I’ll watch literally anything other than a documentary about Ayn Rand,” he begs, but she shakes her head.

“Nope. Now open some chips, Mariano, and let’s get a-watching.”

**

“See, that wasn’t so bad, was it?”

Jess, who has been grimacing for the past couple hours, shakes his head. “Everything I know about that woman, I have learned against my will.”

“Oh, don’t be so dramatic,” she chastises, standing up and stretching.

“You’re a sadist.”

“And you’re five. Now let’s clean up and head back to home base.”

**

They head back to the library. Rory chats excitedly about the documentary and everything she learned from it while Jess mostly listens, appearing to be deep in thought.

“I can watch one about Hemingway with you sometime if it’ll make you feel better,” she offers as they enter the library. She turns around, awaiting a laugh from him, but he’s quiet, running his hand along the edge of one of the tables thoughtfully.

“What’s up?” She asks, frowning a little, concerned.

He swallows. “Did you ever actually like me, or was it all just a mistake?” He asks quietly.

She blinks at him in surprise, completely caught off guard. “What?”

He forces himself to look at her. “I just...I want to know. If it was ever…” He takes a breath. “If it was ever real.”

Rory frowns, finding herself at a loss for words. “I - I don’t-”

“I won’t give you a hard time for telling me you didn’t after I moved to Stars Hollow. I won’t do that. I just need to know if it was ever true or if I was just…” He trails off.

“If you were what?”

He doesn’t answer.

“Jess, you can’t just -  _ do that,”  _ she says, starting to feel frustrated. “You can’t just say something like that and then stop talking.”

“You never answered my question,” he replies in a low voice. “Did you?”

“Jess, I don’t…I can’t…” She stammers. “Why do we have to dig this up all over again? We’ve been doing fine all night!”

“I don’t want to keep pretending like our history isn’t what it is,” he admits. It’s the realest thing about their relationship that he’s ever said to her. “The longer we don’t talk about it,  _ really  _ talk about it, the harder it gets. And we’ve already waited a long time.”

“Jess…”

“So did you?” He asks, a hint of hopefulness in his voice that she can’t quite shake. 

She closes her eyes and takes a deep, shuddering breath. When she opens them, he’s still watching her, expression soft and pained and hopeful all at once. 

“Yes,” she says quietly. “I did.”

He nods slowly, not saying anything for a long time. “So what changed?” He asks finally, voice hoarse.

Rory frowns. “What do you mean, what changed?”

“Well, you don’t feel that way now, right? So what changed? What made you…” He shakes his head and laughs at himself under his breath. “God, I sound pathetic. I told myself I wouldn’t do this, but here we are.”

“You wouldn’t do what?”

“I promised myself that I would never let us lose our friendship because of however we may or may not have felt. And then after the ski lodge, I promised myself that I would move on and I wouldn’t let this torture me.” He laughs again. “But it’s four months later, and all I’ve been able to think about is you.”

Her breath hitches in her throat at his words. She’s still confused, still lost, unsure of how to interpret his words. “Why are you telling me this?”

“Because I’m tired of playing it safe,” he says, with more conviction. “I’m tired of dancing around how we feel. We need to break out of this. Now.”

“If you want to figure it out, then maybe try being straightforward for once in your life!” Rory snaps angrily. “You’ve been  _ hinting  _ at things a lot lately, but you’re still being so unclear!”

“Have I been acting unclear, or are you just too afraid to understand it?” He demands. “You’re so unwilling to let yourself think that I might feel differently than you thought that you think I’m just being confusing, but I’m not. You need to be honest with yourself first before blaming me.”

“I-” She starts to object, but as his words sink in, she draws back. Could he be right? Has she just been hiding behind excuse after excuse rather than facing the truth? “But what about Zoey?”

“What about her?”

“You can’t deny that you messing around with her sent a message that you were done with me.”

“I had just lost the one person in the world that I cared about,” he retorts in a low voice. “I wanted to distract myself, which is something you understand better than most, and you know it.”

“And what’s that supposed to mean?” She demands.

“You know how badly Dean treated you, and you knew you had feelings for me, but you didn’t end it with him for months. You needed a distraction, too, I know you did.”

“That’s different.”

He snorts.

“It is!” She insists. “I was already with him.”

“That doesn’t help your case.”

“Okay, fine,” she snaps. “Maybe it was a distraction, or maybe it was just safe with him, but I had just lost you, too. If you get a break, why don’t I?”

Jess runs a hand down his chin, hesitating. “When you told me how you felt and then stayed with him, it hurt,” he admits, voice softer than before. “It felt like you didn’t care if it was me or him.”

She blinks in surprise. How could he ever think that? “Jess, of course I cared.”

“What’s the difference, then?” Jess demands, stepping closer. “What’s the difference between you and me and you and him?”

“The difference is that I want  _ you,  _ Jess!” She exclaims before she realizes what she’s saying. “The difference is that I want to be with you. I don’t want him. I haven’t for a while now, but admitting that to myself meant that everything would shift, and I was scared. I was terrified of losing that sense of familiarity, and I’m really sorry that you got caught in the middle of that. I am. But the thing is...I didn’t even realize how much I didn’t want him until I realized how much I wanted you.”

The words are barely out of her mouth before he kisses her. 

She finds herself melting into it before she even fully processes what’s happening. His hands cup her face as he kisses her, slow and deep and passionate and earth shattering. When he pulls back, her hands still on his chest, she’s completely out of breath, wondering how it’s possible for just one kiss to calm her and make her heart race all at once.

Rory takes a shaky breath. “Why did you do that?” 

He can’t find his voice for a moment, still breathing heavily. When he finally speaks, his voice is hoarse. “Just...wanted to.”

She purses her lips, swallowing down what she really wants to say. “You shouldn’t have done that.”

His face falls slightly. “What?”

“Jess, we can’t go down this road again. It only ends with us getting hurt and upset and losing each other all over again.”

“It doesn’t have to be like that.”

“It doesn’t have to be, but it just is.” She looks away. “Jess, I like you. I like you a lot, but we might just not work.”

She steals a glance at him, and is surprised to see that his face isn’t pained or upset. Instead, he looks determined, his eyes burning with something she doesn’t recognize. “We can’t know that until we try.”

“We haven’t even been able to get anywhere near a relationship. What makes you think we can do it now?”

“We just...it wasn’t the right time before,” he says slowly. “You were with Dean, and I was too afraid, and then when you were broken up, I was with Zoey, and we just...we couldn’t get the timing right. But our time...maybe it’s now.”

“How can you be so sure?”

“Rory, I have never been sure about anything in my life except you.”

She closes her eyes. They’re on the brink of something wonderful, she knows it, but she’s fully overwhelmed by the fear of losing him. It was horrible the last time, but if it happened again...she doesn’t even want to think about it.

“Look, it only matters if you want this,” he says, and she can hear him moving closer. “If you don’t, just tell me, and I’ll...I’ll let you go. But if you do…”

She opens her eyes. For the first time, his guard is completely down. He’s being honest and real and vulnerable, and it stirs something inside her, something she doesn’t know how to describe. 

“I don’t want to have to keep wondering what could’ve happened if we’d done things a little differently or if we’d met at a different time.” He stops moving to give her enough room. “I want to try.”

“I…”

“I really, really like you, Rory,” Jess murmurs. “I just...I need you to know that.”

She takes a breath. “I don’t want to lose you again, Jess. What happens if we break up? I can’t - I can’t go through that.”

“Then at least we’ll know we had something really good,” he says softly. “But who knows? This...this could be it.”

_ Screw it. _

Rory moves closer until there’s barely any space between them. “Kiss me again.” Her voice is barely a whisper. 

He watches her for a moment to make sure she’s certain before he leans in and kisses her. His arms snake around her waist as he draws her closer, and she stands on her tiptoes, wrapping her arms around his neck. They were so stupid, waiting this long - she thinks she wants to do this forever. 

Forever. It’s scary, yes, but in this moment, she doesn’t think she’s ever heard a prettier word.

**

In the morning, the librarian finds them curled up in one of the aisles, her head on his shoulder and his arm wrapped around her. As they walk to the headmaster’s office, his hand in hers, she thinks -  _ this is the start of a story worthy of Austen and Shakespeare. _


	27. A Room of One's Own

**Summary for the Chapter:**

> Rory and Jess find their footing in their new relationship, but face a roadblock when Jess doesn't call.

Rory pretends not to notice her mom’s knowing looks as they exit the school and get into the Jeep. She tried to act as suspicious as possible when her mom entered Charleston’s office to pick her up, but her mom is picking up on something and definitely can tell that something happened. 

Lorelai turns on the car and then pauses, her hand on the gearshift. “Man, that guy can be scary when he’s angry,” she finally says, making a face. “For a time there I thought he was going to say ‘off with their heads!’ Or something.”

“So, how’d the meeting go?” Rory asks anxiously. She’s had a significant amount of time to explore all the possible punishments she and Jess might be forced to endure, and her mom’s current reaction isn’t helping any. 

“They’re giving you two the rest of the week off and a detention. Monday, after school,” she adds, and Rory groans.

“They’re suspending us?”

“Not suspending, just giving you the rest of the week off.”

“That’s basically a suspension.” Rory’s eyes widen. “Oh, no, is this going to go on my record? Am I going to have a file now?”

“Rory-” Lorelai starts.

“I’m a delinquent now! I _knew_ we should’ve called the police - if we’d done that they would’ve understood, we just lost track of time, but-” She winces when it hits her. “Harvard isn’t going to accept me, not now that I have a _record!”_

“Honey, I wouldn’t worry about it,” Lorelai says soothingly. “It’s just one incident. The only thing he really cared about was the chess set you guys didn’t put back in the right place. Very intellectual, might I add, that you two decided to play _chess.”_

Rory sinks back in her seat. “It’s still a suspension.”

“Okay. Whatever you say, babe.” Lorelai glances over at her daughter. “So…?” 

“So...what?”

“You have to tell me what happened!” Lorelai exclaims excitedly. “You were locked up with _Jess_ all night. Plus, you’ve got that look you get when you have a secret. So. Spill.”

Rory turns pink and avoids making eye contact. “It’s not that big of a deal, really.”

“Oh, please! What happened?”

Rory takes a breath, feeling herself start to smile. “We kissed.”

Lorelai’s jaw drops open. “You _kissed?”_

“Yeah.”

“Was it like a peck on the cheek or like, ya _kissed?”_

“The second one,” Rory mumbles, suddenly feeling very self conscious.

“Is that all you did, or…”

“What do you mean?”

Her mom gives her a look. “Was it just a big makeout session-”

“Oh, my god!”

“-or did you two actually talk?”

“We talked,” she answers. “About...everything that happened. And I think…” She dips her head to hide her smile. “I think we’re going to give it a go.”

“Well, only if Luke doesn’t kill him,” Lorelai adds.

“True. He did _drag_ Jess out of there.”

Her mom smiles. “So...we’re happy about this?”

Rory bites her lip, feeling a little dopey. “Yeah. We’re happy about this. We’re really, really happy about this.”

“Good.” A mischievous expression starts to cross Lorelai’s face. “So, how was the kiss?”

“Mom!”

“What?” She asks defensively. “I have the right to ask!”

“That doesn’t mean I’m going to tell you!”

Her mom sticks out her lower lip.

“That’s not going to work on me.”

“Was it good at least? Well, it probably was, you’ve got that look on your face-”

“What look?”

“The ‘I just got kissed and it was _good’_ look.”

“Just drive, please, I’m begging you,” Rory pleads. She’s sure her face is bright red as her mom snickers.

“Fine, fine. But I’m expecting more information later.”

“Oh, of course you are.”

**

That evening, after she and her mom finish putting away their leftovers from Al’s (he’s branching out into South American cuisine, but not without incident. While the brigadeiro was good, she’s pretty sure she’ll be avoiding empanadas for a little while), Rory sheepishly tells her mom she’ll be right back before grabbing the phone and taking it to her room.

She closes her bedroom door as she dials, sitting down on her bed as it rings. He picks up after three rings.

_“Hello?”_

She can’t help but smile and turn pink when she hears his voice. “Hi.”

_“Hi.”_

“So, um...how are things?”

There’s a pause on the other end. _“Things are good. Luke, uh, he isn’t too happy about everything. The whole ‘locked overnight at Chilton’ thing.”_

“Yeah, he didn’t seem too happy when you left.”

_“I think he pulled my shoulder out of my socket.”_

“Well, you can always ask Kirk to fix it. He just got his CPR certification.”

_“CPR is for when you can’t breathe.”_

“Yeah, but I don’t think he knows that. He keeps asking people if he can give them a checkup.”

_“Free?”_

“Five bucks per appendage.”

Jess laughs. _“Sounds about right.”_

Rory bites her lip - her face is bound to start hurting from the amount of smiling she’s doing. “But, uh, yeah.”

_“Are things...good?”_

“Yeah. Things are good here, too.”

 _“Good.”_ They fall into an awkward silence, but Jess speaks up again after a moment. _“Sorry that I’m sounding like a moron.”_

“Well, you’re not alone in that department.”

 _“It’s just kinda awkward now that we’re…”_ He trails off, sounding unsure. 

She nods before realizing it’s pointless - he can’t see her over the phone. “I think I’m just a little nervous. Even though - and I realize now that I hear it, I don’t really have any reason to be, since we’ve known each other for months already.”

He laughs a little. _“I get it.”_

“So, uh, what’s going on? Like, what were you doing before I called?”

_“Nothing exciting. Just reading.”_

She perks up. “Ooh, what were you reading?”

_“Bukowski.”_

“Which one?”

_Factotum.”_

“Oh, that’s your good mood book.”

He chuckles. _“I didn’t know I had a good mood book.”_

“Oh, you definitely do. Kerouac, too. And Hemingway, unfortunately.”

_“I think Paris’ ears just perked up from 30 miles away.”_

“She’s going to chew you out on Monday.”

_“I think I can handle that.”_

“I’m sorry, have you ever been yelled at by Paris? She could reduce Spock to tears.”

_“Data would be the real test.”_

“One more Star Trek reference and my mom will burst in here and call me a Trekkie.”

 _“And we can’t have that,”_ Jess says in a voice that makes her laugh.

“No, we can’t.”

They fall silent again, but it’s not as uncomfortable as it was before. She settles up against her pillows and brings her knees to her chest. “So...”

 _“What were you guys doing tonight? Before you called and all that.”_ _  
_ “My mom ordered a bunch of food from Al’s, so we just ate and watched a movie. _Say Anything,”_ she specifies, fiddling with the edge of her comforter. Lorelai had vetoed all three of Rory’s ideas, deeming them breakup movies, and insisting that they watch something happy to _celebrate._ Rory blushes at the thought.

_“What’s he doing this week? South American food?”_

“Yep. Although I don’t think he’ll ever be able to top his Chinese food, it was a valiant attempt.” 

_“Huh. I’ve never had his Chinese food.”_

Rory gasps. “You have to! His egg foo young is amazing.”

 _“Well, we’ll just have to get it sometime,”_ he says, and she imagines him smiling.

She blushes. “Yes, we will.”

He clears his throat. _“I had fun with you, last night, by the way. We should get locked up together more often.”_

Rory laughs. “I had fun, too.”

_“Good.”_

Pause. 

“I was just calling to say goodnight,” she begins to say, “if you wanted to get back to your book or-”

 _“No, it’s fine. I like talking to you.”_

She pictures his sheepish smile and her stomach flutters. “Good. ‘Cause I like talking to you, too.”

_“Well, I’d hope so. Otherwise I’d be wondering what the hell you were doing in this relationship.”_

Talking to Jess has always been easy. At the beginning of their friendship, before everything had changed, talking to him felt natural, simple, _right._ And now that they’re here, right where they’re meant to be, it’s somehow even easier, like it’s second nature.

After a while, they say goodnight and hang up, Rory lies back on her bed, feeling giddy. She’ll see him in the morning. 

**

“Uhm, Doose’s.”

“Empty trash can.”

“Flower shop.”

“Gazebo.”

“High school.”

“Uh...oh, inside Luke’s Diner!”

“Hey, you can’t do that!” Rory objects. “And ‘empty trash can’ was a stretch too, by the way.”

Lorelai pouts. “It’s not fair. You got all the easy letters.”

“Oh, excuses.”

“Maybe we should archive the Stars Hollow alphabet game. It gets a little too aggressive.”

“Which is all on you, by the way.”

Lorelai shakes her head. She wraps an arm around Rory, bringing her close as they walk down the sidewalk. “So, you excited to go to Luke’s this morning?”

“Not any more excited than usual,” Rory replies, confused. “Unless there’s a surprise special I don’t know about?”

“Oh, please, you _know_ I’m talking about _Jess,”_ Lorelai says in a swoony voice, earning a glare from Rory. “What? You spent about twenty minutes in front of the mirror this morning and you’re not even going to school.”

“We are _not_ going through this again,” Rory grumbles, taking her arm back from her mother and pulling her jacket tighter around her. 

The door chimes as Rory and her mom walk into the diner. Lorelai grabs a table, beating Kirk to the punch, much to his dismay. Rory sits down at a more leisurely speed, taking off her jacket and draping it over the back of the chair. Once they’re both seated and Lorelai has successfully fended off Kirk, Luke comes over to take their order.

“Morning,” he grunts, in typical Luke fashion. Lorelai perks up, picking up on a prime opportunity to give him a hard time. 

“Well, you’re pleasant,” she teases. “And gee, I was planning on going easy on you today, but after this abysmal greeting…”

“Ignore her,” Rory cuts in. Lorelai gasps in mock offense. “She’s in a bad mood since we decided to ban the Stars Hollow alphabet game.”

Luke looks at the two amusedly. “Are you going to order, or should I go check on my other, more patient customers?”

Lorelai gasps again. “No, don’t go! If you go, I won’t get my coffee, and if I don’t get my coffee...oh, it’ll be dark, trust me.”

“Fine. But hurry up - I _do_ have other patrons.”

As Lorelai orders, Rory can’t help but glance over in the direction of the curtain a few times, trying to hide it behind a menu but failing miserably. As Luke collects their menus, he frowns when he notices. “You okay there, Rory?”

“What? Oh, yeah,” she says, blushing. “Yeah. I’m just…”

“Say, Luke, where’s Jess?” Lorelai pipes in, saving Rory from having to finish her sentence. 

He looks between the two, a little puzzled, but moves past it. “He _should_ be down in a few minutes, if he decides to grace us with his presence and actually do the work he gets paid to do.”

“So, a 70/30 chance.”

“That’s generous,” Luke snorts. “I’ll be back with your coffee soon.”

“You’re my hero!”

Luke retreats back to the counter to give the order to Caesar. Lorelai turns to Rory with a mischievous grin, but Rory holds up a hand to stop her.

“Don’t.”

A few minutes later as Rory is sipping her coffee, there’s a rustling as Jess pushes past the curtain and Jess enters the diner. Rory, startled, chokes on her coffee. Lorelai snorts. “Smooth.”

Rory shoots her mom a dark look before setting her cup and straightening up when she notices Jess approaching. 

“Hi,” he says with a nod, hanging back a foot away from the table.

Rory bites her lip, trying to contain a grin. “Hi.” She turns back to her mom. “Can I…”

Lorelai nods. “Go. But be back soon so you can watch me do my waffle bit with Luke.”

“Thanks,” Rory says breathlessly before getting up and grabbing her jacket. She hurries out of the diner, Jess close behind. She doesn’t look back until she’s rounded the corner, stopping behind the diner just out of sight of the windows. She leans up against the wall as Jess approaches her, smiling.

“So, here we are,” she breathes.

He dips his head in acknowledgement. “Here we are.”

“How’d you sleep?” Rory asks, and then cringes, knowing how _stupid_ her question sounds - the awkwardness from the beginning of their phone call the night before seems to be back with a vengeance.

Fortunately, Jess doesn’t seem to mind. “Well enough, I guess,” he answers with a shrug. “Although Luke woke me up at around five.”

“On purpose, or…?”

“Most likely unintentional. He knocked over something in the bathroom.”

She pulls her sweater over her hands, only making eye contact in small amounts. “Guess you two are living in close quarters, huh?”

Jess laughs. “You could say that. He’s either considering moving or tearing down the wall and expanding.”

“Well, he’d have to buy the building next door to do that.”

“I pointed that out to him, but he ignored it. He may be planning to commit a crime.”

“I’ll visit him in prison.”

“He’ll appreciate that.” Jess rocks back and forth on his heels once for a lack of anything better to do. “How about you?”

“Oh - good, good. I slept...good.” 

Pause. 

“Guess we’re still a bit…” He trails off.

Rory nods. “A little.”

“So, let’s just...regroup.”

“Regroup.”

He takes a step closer, uncertain, before taking her hand in his and lacing their fingers together. He rests his other hand on the wall behind her. Her gaze meets his, and she smiles, face heating up under his unwavering stare. 

Jess hesitates for a moment before he leans in and kisses her, soft and sweet. She allows herself to get lost in it, her hands sliding up his shoulders as she deepens the kiss. His now free hand travels down and rests on her hip, and he presses closer, leaving no room between them.

When he eventually pulls away, her eyes remain closed for a moment. “I could get used to that,” she murmurs, and he laughs.

“You know what? Me, too.”

When she kisses him again, they’re both smiling. 

**

Lorelai glances out the window as Jess and Rory walk away and out of her line of sight. Luke, who promised her coffee, has gotten distracted by the counter, reprimanding Kirk for something she can’t quite make out. Figuring she might as well get the _telling_ over with, she gets up and goes over to the counter and sits down on one of the stools.

Luke frowns when he notices her. “Do you not trust me to remember to bring you your coffee?”

“Hey, you’ve forgotten before,” she argues. “But no. That’s not what this is about.”

“Can it wait?”

“Yeah, yeah, you’ve got customers. Just listen, for like, a second,” Lorelai insists. He mutters something under his breath, but complies. “Look, I just wanted to tell you this before you heard it from anyone else and went insane.”

“Insane, what - you know what? Just tell me so we can move on quickly.”  
Lorelai hesitates, trying to decide how to phrase this. “You know how Jess and Rory got locked up in Chilton overnight?”

“I _was_ the one who had to pick Jess up at six in the morning,” Luke says in confirmation. “Speaking of Jess and Rory - what’s up with them leaving the diner together like that?” He asks, using his thumb to gesture in the direction Jess and Rory went. “Schoolwork or something?”

“Not exactly.” Lorelai takes a breath. “Rory and Jess are together.”

She holds back a laugh as she watches Luke process her words, appearing to go through the five stages of grief quite quickly. “They’re _what?”_

“They’re together,” Lorelai confirms. “As in, dating. Going steady. Courting. Should I go get a thesaurus so I can continue.”

Luke holds up a hand to stop her. “Alright, alright. But they’re - they’re _dating?_ Since when?”

“They kissed when they were stuck at Chilton.” She rolls her eyes when she notices the vein in Luke’s forehead. “Relax, Luke. Nothing happened. I already asked.”

He eases up a little at that. “Fine. As long as you’re sure. I just…” He laughs a little under his breath. “Rory and Jess are dating?”

“Rory and Jess are doing _what?”_ Babette exclaims from a couple tables away. Luke cringes and gives Lorelai an apologetic look. 

“Nothing, Babette,” Lorelai assures the other woman, but Babette doesn’t appear to buy it. 

“No, you said they were dating. I can’t believe this - Rory and Jess, _dating.”_

“It’s about time,” Miss Patty says. “Ever since that young man moved to town, those two have been exchanging some M-rated glances all over town.”

“Okay, Patty-” Lorelai starts, but she gets cut off.

“You know, I always thought it would take a little bit longer for them to get together,” Kirk chimes in. “I was about a week off. Damn.”

“Kirk-”

 _“I_ didn’t think it would happen,” Reverend Archie claims. 

“Jess is always so quiet,” Rabbi David amends in agreement. “He never really talks to anyone, let alone our Rory.”

Andrew gapes at them. “Are you kidding? Jess practically lives in the bookstore. It’s as if they were made for each other!”

Miss Patty nods wisely. “I honestly had no idea what to expect when Jess came into town, but he’s a lot less trouble than he looks. Just the right amount, especially for Rory, no?”

(If she’s being honest, Lorelai gets what she means - in any other situation, Jess would probably be terrorizing the town with dumb pranks, but from what she knows, he moved to town to escape some pretty sucky circumstances. It seems as though he has some respect for the town that’s taking him in. And Lorelai can’t say she hasn’t been there.) 

The chatter continues as the townspeople excitedly exchange opinions and admit if their predictions were true or not, but it all suddenly subsides as the door chimes and Jess and Rory step inside. The townspeople watch the two with bated breath in a way that’s almost laughable.

Rory looks around, looking absolutely bewildered. “We’re back?” Everyone stays silent. “Yay,” she adds, looking to Lorelai for clarification. 

_They know,_ Lorelai mouths.

Rory grimaces for the rest of their meal. 

**

Rory and Lorelai leave the diner sooner rather than later, Lorelai apologizing profusely for all the stares and questions being directed at her daughter. Jess goes to kiss Rory goodbye, but under the watchful eye of the town, he stops himself, settling for a smile and an “I’ll call you tomorrow” before the two women leave. 

Luke looks between the door and Jess a couple times before telling Caesar he’ll be right back, grabbing Jess by the arm, and dragging him behind the curtain and up the stairs.

“What the hell?” Jess objects as Luke lightly shoves him into the diner and closes the door. “Does Bedlam know that you escaped, or do I need to make a phone call?”  
Luke breathes heavily for a moment before pointing to the kitchen table. “Sit down.”

“What?”

“You and I need to have a chat.”

Knowing it’s probably pointless to antagonize Luke in his current state, Jess complies and sits down at the table. He clasps his hands in front of him and sits up straight. Luke gives him a look. 

“Knock it off.”

Jess relaxes in his chair and waits.

Luke begins to pace a bit, looking a bit wild as he does so. He finally stops, turning to face his nephew again with a humorously serious expression on his face. “I know that as a teenager, you’re bound to start wanting to...date, at some point. And when you do that, there’s going to be some ground rules that you have to follow to stop certain _things_ from happening.”

“What-” And then, it clicks. “Lorelai told you,” Jess answers for Luke, a grimace on his face.

“She did. So, now, we have a talk.”

Jess rolls his eyes. “I’ve already been given the ‘birds and the bees talk,’ if that’s what this is about.”

“This isn’t a joke, Jess.”

“Au contraire, Uncle Luke. From where I’m sitting, this is hilarious.”

“Hilarious, huh?” Luke’s eyes narrow. “This is serious business, Jess. Now that you’re starting to date girls - no, not just girls, _Rory_ \- some rules have to be put in place.”

Jess briefly considers telling Luke that he’s already _dated,_ but figures that the consequences wouldn’t be worth it, so he keeps his mouth shut. 

“On weekdays, you will have her home by nine. On weekends, you will have her home by eleven. You will not smoke, you will not drink, you will not do drugs, and you will not _think_ about smoking or drinking or drugs.” Luke resumes his pacing. “You will only go in a 1,000 foot radius from the diner. You will not leave the town. You will only go places where other people are around. Do I make myself clear?”

“Sure. May I speak now?”

“If you must.”

Jess gives his uncle a once-over. “Are you okay? You know...mentally?”

Luke glares at him. “This is for your own good, Jess. You may not think much of it now, but you do not want to get into trouble with this girl. Unless you want your head up on Lorelai’s wall.”

Jess grimaces at the imagery. “And what type of trouble exactly are we talking about here?”

“You _know_ what type of trouble I’m talking about.”

“No, actually, I don’t,” Jess replies seriously. “Tell me what this _trouble_ is that is obviously giving you an aneurysm just to think about.”   
Luke opens his mouth as if to speak, but nothing comes out. Apparently, he didn’t anticipate how uncomfortable the conversation could get if it was turned around on him.

Jess snorts. “Luke, we’re sixteen. We’re going to go to the movies and the bookstore and get burgers. No museum heists, no gang wars, nothing resembling _Maitresse_ or _Waitress._ So I think you can breathe before you pass out.”   
Luke stares at his nephew for a moment, most likely assessing the sincerity in Jess’ claim. “FIne,” he relents, “but if you even _think_ about going back on that, there _will_ be consequences.”

“Sure.” Jess gets up from his chair. “We’ll assess when we’re seventeen,” he says, clapping Luke on the shoulder before walking over to the table where his books are stacked.

“What - no, we will not. Jess? Do you hear me?”

“Loud and clear.” Jess picks up one of the books, turning it over in his hands before setting it back down. From the corner of his eye, he sees Luke walk over to the couch and sit down.

“So, you know what tomorrow is, right?”

Jess glances to the left briefly before focusing back on the books. “Yep.”

“Are you gonna want to, uh…to-” 

“It’ll just be like any other day,” Jess interrupts firmly. 

Luke nods, albeit appearing a little unconvinced. “Okay.”

“Good.” Jess clears his throat and turns away from the books. “Now, if you’ll excuse me, I have a bank heist to assemble.”

“Jess.”

“Gang meeting?”

“Jess.”

“I heard the local dominatrix just moved back to town.”

Luke shakes his head, exasperated. “Just go back to work, okay?”

“Fine. But just be warned, I have a large shipment coming in at three. If it looks like cocaine, don’t worry - it’s...well, let’s go with crushed up baby aspirin.”

“Out!”

**

The next day, Jess doesn’t call.

Rory keeps by the phone, excitedly waiting for it to ring, but as the day goes on, she gets more and more deflated. The only call they receive is Kirk advertising his new fish store - out of his mother’s living room, of course - but nothing from Jess.

She can’t mope all day, though, because as they do every friday, she and her mother have to go to dinner. She gets dressed, doing her best to ignore her annoyance with him. He said he would call. So why hasn’t he?

**

“What’s on your mind?”

Rory stares out the window, watching the trees by the side of the highway pass by in a blur. “Nothing.”

“Okay, we both know that that is a bold-faced _lie,”_ Lorelai teases. “Come on. You’ve been brooding the entire car ride.”

“Hey, I have not been _brooding.”_

“Tell mommy what’s going on in that big brain of yours.”

Rory makes a face. “I hate every single part of that sentence.”

“If I repeat it over and over will it make you tell me?”

Rory rolls her eyes, but there’s no real malice behind it. “It’s just that...it’s kind of stupid, now that I think about it, but-”

“I have moped about _many_ stupid things in my day,” Lorelai reminds her. “Including the fact that Nick Lachey could never be my husband.”

“Really? Not Drew?”

“So, what’s up?”

Rory sighs, resting her head up against the back of her seat. “It’s just that Jess said he would call. And he hasn’t.”

Lorelai nods slowly. “Well, did you call him?” She asks after a moment.

“No, but that’s because _he_ was the one who said he’d call. So the responsibility of reaching out is on him today, not me. If _I_ had been the one to promise to call, _then_ I would call. But since he said he would, he has to make the first move.”

“As much as I understand the teenage girl logic here, I have to point out - this issue isn’t going to resolve itself.”

“I know. But…” She bites her lip. “Maybe he has a really important reason for not calling.”

“What, like he got kidnapped by the Connecticut mafia or something?”

“Maybe.”

Lorelai gives Rory a sympathetic look. “He definitely should’ve kept to his promise, I won’t argue that. But don’t harbor resentment for too long. Confront him about it at some point or other, and soon. Make it clear you expect a call when one is promised.”

“Okay.”

“I have a feeling it’ll all work out.”

Despite the situation, Rory smiles. “Thank you, mom.”

“Hey, anytime. But it’s on you if it doesn’t work - you should know better than to go to _me_ for romantic advice.”

Rory stifles a laugh. “Noted.”

**

Jess’ cell phone rings, startling Jess out of his stupor. Today, he’s been finding it hard to do anything, really, even if he’d insisted he would be fine. He still owes Rory a call, and he knows this, but something has held him back all day. Part of him wonders if this is her, but he wouldn’t blame her if it wasn’t - he _was_ the one who promised to reach out. She owes him nothing. 

He sits up, reaching out for his phone and answers it. “Hello?”

_“Hey.”_

He smiles a bit when he hears his friend’s voice. “Long time, no call.”

Zoey laughs. _“Things have been a little busy around here as of late. I heard you got locked in the school overnight?”_

“Oh, jeez. How far has that rumor spread?”

_“Far enough, I’d say. But don’t worry, I’m sure something far more interesting will happen, like, tomorrow.”_

“Very likely. I’m nowhere near the most dramatic.”

_“You’re kinda boring like that.”_

He laughs under his breath. “So, what’s going on?”

_“I just...I remembered what today was, so I wanted to reach out, see if you were okay and all that.”_

“Oh.”

_“Yeah. So...are you?”_

Jess exhales slowly. “Okay as I can be, I guess,” he says finally. “And don’t give me any Doctor Phil bullshit here, because I’m being honest.”

_“Damn. I googled three new psychological terms for this.”_

He rolls his eyes good-naturedly. “Such a shame you won’t get to use them.”

She _tsks. “Is your uncle doing okay?”_

“Well, he’s getting through the day, so that’s something,” Jess replies, not without a bitter tone. “He’s lost family before, though, so I guess he knows the drill.”

_“One year since your mom died...I’m sorry, Jess. I didn’t say that yet, but I am. To put it simply...it sucks.”_

He nods a bit. “It does.”

_“Do you need to talk at all? I can always lend an ear.”_

“It’s fine. Thanks, though, you know. For asking,” he adds as an afterthought. “I...didn’t expect you to. But it was nice, so...thank you.”

_“Of course, Jess. We’re friends, remember?”_

“Part of me wondered if we’d really stick to that promise after we ended things,” he admits. 

Pause. _“Jess, that is - and you’ve said a lot of depressing things in our short time together, trust me - one of the saddest things I’ve ever heard you say.”_

He lets out a laugh. “Fierce competition?”

_“Wins by a landslide.”_

“Yeah, well…” He shakes his head. “I’m glad I was wrong.”

He can hear her smile in her voice. _“Yeah, me too.”_

“I think I’ll be fine,” he tells her after a moment of silence. “It’s not like I was close with her. She was never really a mother to me.”  
 _“Even then...it’s still a loss.”_

“I guess.” He bites his lip. “But enough about me.”

_“Very humble. I suppose you’ll ask how I’m doing?”_

“Something along those lines.”

 _“I’m doing quite well, actually,”_ she begins. _“We’re ordering pizza tonight. Made my entire day.”_

“Oh, I’m sure.”

 _“Speaking of - the doorbell just rang, so I think it’s here.”_ He hears some rustling on the other end as she moves. _“Which means I must cut this call short, unfortunately. But I hope you’re doing okay, Jess. And again, I’m always here. You got that?”_

The corner of his mouth turns up. “Yeah. I got that.”

_“Good. I’ll see you Monday!”_

“See you Monday.”

When he hangs up, he feels just slightly better. 

**

Once they drive past the _Welcome to Stars Hollow_ sign, Rory has made up her mind. When they turn onto the main street, she asks her mom to drop her off outside the diner. 

“I’ll meet you at home,” she assures her mom as she gets out of the car.

“Alright. But don’t be terribly long, dear - Grandma wore me out tonight and I _must_ watch something with you to heal. _Next Generation_ marathon on NBC sound good?”

“Most intriguing, captain,” Rory says in confirmation.

Lorelai drives off in the direction of home, but Rory walks towards the diner. Luke is cleaning tables inside, so she knocks. He hurries over to open the door.

“Hey, Rory.”

“Hey, Luke,” she greets. “Is Jess around?”

“He actually just left,” he says apologetically. “If I’d known you were coming over…”

“It’s okay - this wasn’t planned or anything. I just…” She swallows. “Do you know where he is?”

Luke shakes his head. “He said he was going ‘out,’ if that helps at all.”

“Oh.”

“Sorry,” he adds apologetically.

“It’s fine,” Rory assures him, “really.” Pause. “I have a feeling I know where he is, anyway.”

**

She goes to the bridge.

It’s been overcast all day, so when it starts to drizzle, she isn’t surprised, but she quickens her pace, not wanting to get caught in some downpour. She gets to her destination fairly quickly, and sure enough, she can see a faint outline of someone sitting on the bridge. 

She slows down as she approaches him, as if she’s afraid of spooking him. He doesn’t look up, but he shifts a little, and she’s sure he notices her. 

“You didn’t call.”

Her voice feels loud in the quiet of the evening. Jess takes a deep breath, fiddling with an unlit cigarette.

“I’m sorry.”

“Why didn’t you?”

He doesn’t answer. There’s a clap of thunder, and the rain begins to pick up, plastering her hair to her face. She tries to stay patient, but it gets harder and harder the longer she stands out in the rain. “Jess, please.”

She can’t help but notice the tick in his jaw as he stares out into the water. “I’m sorry,” he says again. 

“Jess, I need to be able to rely on you,” she says, fighting to keep her voice even. “When you say you call, you call. I need to be able to count on that.”

“I know.”

“So why didn’t you?”

He’s silent again, and for a horrible moment, she considers just turning on her heel and storming away. But she stays rooted in place, even if it’s raining even harder and she’s soaked. 

“Can we go inside and talk?” He asks quietly.

“No,” she hears herself say. “No. We’re talking about this here and now or not at all.”

He nods. She waits as he puts the cigarette back in his pocket and stands up to face her. _Patience. Be patient._

“I waited all day,” she begins, her voice wavering slightly. “I stayed inside and I waited for you to call. I waited, and you never called.”

He watches her, jaw set. 

“Is this not something you want?” She asks, voice small. “Are you having second thoughts about...about us?”

“No!” Jess exclaims, almost frantic. “No. Of course not.”

“But-”

“Do you have any idea how long I’ve wanted this? Wanted you?” He shakes his head incredulously. “Rory, I have spent the last eight months hoping for just a chance to have this, here, with you. And I just...I would never want you to think that that’s not what I want.”

“Then what’s going on?” Rory asks, her voice growing louder as it rains even harder. “Why didn’t you call?”

He breathes in and then out, slowly, as if steeling himself, keeping himself steady enough to tell her the truth. “It’s been a year,” he says. “Since...since Liz died. And I just…”

Suddenly, it makes sense. Why he didn’t call, why he was so hesitant to admit it. “Jess…”

“It’s not an excuse,” he presses on, “and I know that. I should’ve kept to my word. I thought I would be able to, and then…”

She shakes her head. “No. No, I get it. I...I’m sorry, Jess. I guess I should’ve waited to get angry, because that - that is so understandable and a valid excuse, and...I’m sorry.”

“I’m the one who should be sorry. I never want to make you doubt how I feel about you.”

“It’s not your fault.”

He opens his mouth, as if he wants to speak, but nothing comes out. But she thinks she gets it. The same words are stuck in her throat, fighting to be said. It’s scary, but she wants to tell him, more than anything. She just needs to take a leap of faith. 

“Jess, I want…” She swallows. “I need...I…”

He furrows his brow in concern. 

She closes her eyes for a moment. When she opens them, their gazes meet, and suddenly - suddenly, it isn’t so hard.

“I love you.”

His breath hitches in his throat. He’s quiet, unmoving, but it’s so different than it was all those months ago at the ski lodge. She has no expectations, no pressing need for reciprocation. It’s enough for him just to know. 

“I love you. I’m - I’m in love with you. And you don’t need to say anything, Jess, really, I just…” She smiles a bit. “I don’t want _you_ to think that I don’t want this, either. Because I do. So much.”

Jess watches her for a moment, blinking, but she thinks she sees the ghost of a smile on his face. 

“I love you. Did I mention that enough?” She adds with a laugh.

He steps closer, cupping her face with his hand, his thumb brushing her cheek. “I’m going to kiss you now,” he murmurs before leaning in and capturing her lips with his.

In that moment, nothing else matters, except for the fact that he’s kissing her. It doesn’t matter that it’s pouring rain, or that her clothes are soaked all the way through, or even that they’re on a bridge with no protective railings and one wrong step could have her falling into the lake. None of that matters, not when he’s kissing her like this. 

She’s unsure how long it’s been when she pulls back, pressing her forehead up against his and catching her breath. But then he kisses her again, and the rest of the world falls away. 

**Notes for the Chapter:**

> One more chapter left...


	28. In Our Time

**Summary for the Chapter:**

> As the school year comes to a close, one chapter ends while a new one begins.

**Notes for the Chapter:**

> Wow. The last chapter. I just want to thank all of you for your kudos, comments, and general support with this fic. This fic has been very important to me these past several months, and I'm really glad that I got to share it with all of you. It had been in the works for a while, and now it's over. Crazy!
> 
> This won't be the last time you see me, though, for better or for worse - I'm very excited to plan out my next one. It might be a little while until it's ready, but I hope you all stick around for it.
> 
> Again, thank you so much for reading. I hope you enjoy the final chapter.

“Jess, we have to go,” Rory gasps in between kisses, her hands gripping at the hair at the nape of his neck. “We only have half an hour before we have to go to school.”   


Jess’ hands wander down to her hips and he lifts her up, setting her down on the table that is pushed up against the wall. “School? We have school today?”

She laughs a little at the vibrations against her neck from his voice. “If we want to have enough time to eat, we really should stop.”

“I agree.”

He kisses her again. She lets out an involuntary moan, wrapping her arms around his neck to bring him closer. When she pulls back to breathe, he trails kisses from her jaw to her neck. She breathes out, running her hands up his arms to his shoulders. 

“Come on,” she says, but it comes out as more of a whine when he focuses on that one spot that drives her insane. 

“One more minute.”

She sighs blissfully, her hands trailing back up into his hair. “Jess.” 

He pulls back long enough to shush her before kissing her again. She allows herself to disappear in it for a moment, but then she breaks apart from him, resting her forehead against his. 

“Jess-” He kisses her. “As wonderful as this is-”

“Oh, so this is  _ wonderful?”  _ He teases before planting a kiss on her forehead. 

She turns pink. “As wonderful as this is, we have to go. Sneaking around and having secret makeout sessions in Miss Patty’s can only last so long.”

He laces their hands together, and he’s  _ so _ close, so so close, it would be so easy to kiss him again, he’s right there - but she holds herself back, relishing in the feel of his hands in her own. 

“I like this a lot more than school,” he murmurs, and she laughs. 

“I know, but we don’t have a choice.”

“And may I remind you that taking a detour to Miss Patty’s was  _ your  _ idea.” 

She sighs. “Yes, but so is getting my education so I can get into Harvard and-” She kisses him chastely. “Maybe, if my schedule allows it, we can meet up again during lunch for more of this.”

He raises an eyebrow and grins. “Oh, yeah?” 

She smiles, blushing a little. “Yeah.”

Jess kisses her again, moving his hands to her hips so he can pull her closer. She wraps her legs around him and brings him closer until there’s no room between them, but he’s never close enough, it’s never enough. She doesn’t understand how kissing Jess is so overwhelming but always leaves her wanting more. 

Eventually, he’s the one who stops it, turning their kisses more chaste until he pulls away completely. “So, leaving. We have to leave.”

“Yes, we do.”

He brushes his nose against hers a couple times before releasing her from his arms and stepping back. She smiles at him and hops down from the table. 

“Our first day back,” Jess says after a moment of silence. He leans up against the table, his hands supporting him. 

“Our first day back.”

“And our first day at Chilton after we started dating.”

Her face heats up ever so slightly. “That it is.”

“We haven’t really talked about that.”

“No, we haven’t.” 

Jess hesitates, drumming his fingers on the underside of the table. “We’re not keeping it a secret around town.”

“Right.”

“So…” 

“So?”

He heaves out a sigh. “Are we going to keep it a secret at school?”

_ Oh.  _ She wraps her arms around herself, thinking over his question. “Maybe we should,” she says finally, “not because I want to hide it or anything, but because of-”

“Tristan,” he finishes for her.

She nods grimly. “Yeah.”

Jess thinks about it for a second, and she watches the tick in his jaw nervously, waiting for him to start yelling. Instead, to her surprise, he just nods. “We need time to figure out how we’re going to deal with him, anyway.”

She sighs in relief. “That’s exactly what I was thinking.”   


“But you agree that we’re not keeping it a secret in Stars Hollow, right?” He clarifies, a note of uncertainty in his voice.

“Right.”

“So…” He swallows. “And don’t get me wrong, I’m enjoying this immensely, but if we’re not hiding it, why are we sneaking around?”

“What do you mean?”

“The secret makeout sessions in the dance studio, the shed behind the inn, behind Weston’s...it kind of feels like we  _ are  _ hiding. At least, hiding from someone.”

“Oh.” Rory bites her lip, afraid to look him in the eyes, because if she had had this conversation with-

“Dean.” Jess watches her, waiting for her affirmation. “We’re hiding from Dean.”

“I just...I don’t know how he’s going to react,” she admits, giving Jess an apologetic look. “I mean, he was already really angry when he  _ thought  _ I dumped him for you, but now that we’re actually together...he’d be really mad.”   


Jess clenches his jaw, and she waits anxiously. Jess is so different from Dean, and she knows it, she does, but after everything that happened with Dean - his jealousy, his temper, the horrible breakup - the remnants of that relationship still linger. 

Finally, Jess speaks, his words careful and considerate. “I get it,” he begins, and she can breathe. “I just...I want to be able to kiss you in places that aren’t dark or dusty or covered in cobwebs.”

She smiles. “I know. And we will soon, I promise. This is just like the situation with Tristan. I need time to figure out…”

“How you’re going to deal with it,” he suggests, and she nods. 

“Exactly.”

“I guess I can live with that,” he relents, playing with her hand in his. 

Rory grins wider and kisses him again, lingering a little longer than necessary. “Thank you,” she murmurs.

He shrugs. “No biggie.”

“No. Jess-” She bites her lip. “It is a big deal. You doing this for me, being patient...it means a lot. Really. So thank you.”

He watches her for a moment before he smiles in return. “Of course.”

“Now, we should go,” Rory instructs, peeking out of the windows. “But one at a time, so no one suspects anything.”

He shakes his head in amusement and follows her towards the door.

**

Rory enters the diner first, hoping against hope that her face isn’t too flushed or her hair too askew. Her mom eyes her shrewdly as Rory sits down at the table, shrugging off her jacket and draping it on the back of the chair. 

“So, where were you?” Lorelai finally asks. 

Rory squirms under her mom’s gaze. She does her best not to act suspicious, but she’s sure she’s failing, and miserably at that. “Nowhere special. I was just - I was caught up. Talking. To Babette,” she adds. 

To Rory’s relief, Babette isn’t in the diner when Lorelai glances around the room. “And what, praytell, were you talking about?”

“Well, you know Babette. She wanted to know the  _ scoop  _ about me and Jess, and I told her - I told her that, that, uh…” Rory winces. “Okay, I give. You got me.”   


“It’s not your fault you’re so terrible at lying,” Lorelai coos, earning a glare from her daughter. “You were with Jess, I take it?”

Rory nods. Lorelai shakes her head knowingly. 

“I can’t say I can blame you. You  _ are  _ your mother’s daughter after all - take advantage of that honeymoon phase. Although, don’t-”

“Take  _ too _ much advantage, I know, I get it,” Rory interrupts, face red. “You know, one of these days you’re going to run out of those clever euphemisms. Please, get them out of your system - I’ll give you two minutes.”

“Which was exactly the length of your conception.”

“Oh, gross!”

The door chimes again and Jess walks in. Rory has to admit, he’s doing a much better job at the whole nonchalant thing than she did. 

“And where were you?” Luke more or less demands.

“Doose’s,” Jess replies without missing a beat. “You said you needed more lettuce.”

“And where’s the lettuce?”

Jess holds up a bag that Luke (and Rory, for that matter) surprisingly missed. 

“Fine,” Luke grumbles, taking the bag from Jess and ducking into the kitchen.

“I’m expecting reimbursement!” Jess calls after him.

Lorelai turns to Rory, looking quite entertained. “Man, he’s  _ good  _ at this. Backed up the alibi and everything.”

Rory laughs under her breath. She watches Jess grab the coffee pot and start refilling the customers’ cups. He glances over and catches her gaze for a moment before turning his attention back to Kirk’s coffee mug. “Yeah, I guess he is.”

**

Jess offers to drive Rory to school, but she declines, reminding him that they’re keeping their relationship on the  _ downlow  _ \- a phrase that makes him laugh and kiss her quickly before relenting. She’s quite stubborn, but he’s always liked that about her, ever since they met. 

Jess parks in the student parking lot, resisting the familiar temptation to scrape Tristan’s familiar black car. As he makes his way towards the iron gates and then through the courtyard, he keeps his head down, knowing that he’s about two seconds away from breaking out into a grin. This Gilmore girl, and the things she does to him. He doesn’t know if he’ll ever understand it. 

He stops at his locker first. He needs to put away his jacket and grab the textbooks he probably won’t end up opening. He also, after a moment of hesitation, adds the book that Mr. Medina assigned a couple weeks prior to the contents of his messenger bag. 

“Knock knock.”

Jess jumps a little when Zoey appears, seemingly out of nowhere, leaning up against the locker next to his. 

She laughs. “You’re jumpy.”

“Hey, this isn’t news,” he reminds her. He shuts his locker door and turns so he can fully face her. “Nice to see you.”

“It’s nice to see you, too, especially after you got  _ suspended,”  _ she teases. “Man, I can’t believe you and Rory got locked in the library overnight. It’s like your very own bottle episode.”   


“Well, not exactly. We had access to the whole school.”

“Did you get test answers?”

“Okay, think: Rory Gilmore, getting test answers. What do you think?”

“Ah, damn,” Zoey says jokingly, snapping her fingers. “Guess I’ll ask someone else.”

Jess shakes his head, amused. He leans his back against the locker, resting his foot on the one below his. “How was school without me?”

“Dull. I was so lost without your stupid literary jokes.”

He laughs, and her eyes narrow suspiciously.

“You’re happy. Why are you so happy?”

“Am I not allowed to be in a good mood?” 

“You’re allowed, but you’re never actually  _ in  _ one.” She eyes him, trying to put the puzzle pieces together. “What’s going on?”

“I can  _ hear  _ the cogs turning in your brain.”

Zoey is quiet for another moment as she stares at him, and then she gasps. “Oh, my god! You and Rory got together!”

“Say that a little louder, will you?” Jess hisses. “I don’t think Headmaster Charleston quite heard that.”

Zoey, undeterred, squeals and slaps him in the chest. “This is amazing! Isn’t this amazing?”

“I guess,” Jess says, but even he can’t bite back the grin that’s spreading across his face.

“Oh, my god!” Zoey repeats, awestruck. “Jess, I’m so happy for you!”

“Okay, calm down.”

“I knew it would happen eventually, but this-” She jumps up and down. “You’re together!”

“Yes, I am aware.”

“And you’re in love with her. Did you tell her? Did she say it? Who said it first?” Zoey demands, talking a mile a minute, her eyes wide. 

Jess rolls his eyes. “You’re  _ way  _ too invested in my love life.”

“Tell me!”

He presses his lips together and hesitates. “She said it,” he finally says, “but I...I do, you know I do, but the words…”

Zoey waves a hand in dismissal. “You’ll get there. It’s still so great!”

“You’re scaring me a little here.”   


“When did it happen? Was it when you two were stuck in the school?”

“Yes, it was. Now, I’m going to try to not be late to the one class I can tolerate, so if you don’t mind…”

“No worries. I can multitask.” She walks alongside him, still smiling brightly. “Jess, seriously, I’m so happy for you. You deserve this.”

He shrugs. 

She elbows him in response. “Oh, stop it. You do. You two are perfect for each other, and you know it.”

“Just keep this quiet, would you?” He asks. “Rory and I agreed to keep it to ourselves for a little while. We don’t want it getting out.”

Zoey nods in understanding. “A wise decision. The rumor mill here, it’s ruthless.” The bell rings. “Okay, I’ve gotta get to math class. But I’ll see you later?”

Jess nods. “Sounds good.”

Zoey smiles. She goes to leave, but stops herself and faces him. “This is good, Jess. It’s good.”

He fidgets a bit, unsure of what to do with the happiness he’s feeling. “Yeah. It is.”

She winks, turns around, and walks towards her class while Jess bites back his smile.  _ This is good, _ he repeats to himself. For once in his life, he isn’t just sitting there, waiting for the other shoe to drop. So, he walks into Mr. Medina’s classroom with an uncharastically bright look on his face. It feels so strange, to be this goddamn happy - but he thinks that maybe, he could get used to it.

**

“Rory.”

“Yes, Paris?” Rory asks warily, closing her locker and shifting so her books don’t fall out of her arms.

“So I just have to hear it from the grapevine that you and Balboa Jr. got locked up in the school overnight?” Paris demands. 

“I was going to tell you, I swear, but the Chilton rumor mill works a lot faster than I do.”

“Are you going to tell me what happened, or do I just have to stand here and wait for you to take a hint?”

Rory lets out an exasperated sigh. “Paris, I don’t know what to tell you. We were locked up overnight, and now we’re not anymore. Okay?”

Paris eyes Rory suspiciously. “Something’s different about you.”

“Well, I am trying a new moisturizer.”

Paris rolls her eyes. “Spare me the standup routine, okay?”

“Nothing happened!”

“And you’re sure that’s the answer you want to go with?”

“Paris, I swear!”

Paris tilts her head to the side. “It’s just that you, and Jess, spending hours alone...some would say that’s the perfect time to air out dirty laundry and get down to business.”

“Jeez!”

“So?”

Rory does her best to withstand Paris’ intimidating stare, but after a minute, she can’t keep going. “Fine, I give!” She exclaims. “We kissed. We kissed, and now we’re dating. Are you satisfied?”

A smug smile spreads across Paris’ face. “Well, I’ll be damned. You and Mariano finally got over yourselves and worked it out, huh?”

“If you want to put it that way, sure.” Rory huffs. “Is the interrogation over? Can I go?”

Paris considers this. “Mm...not yet. There’s a few more topics I want to cover.”

Rory groans. “God help me.”

Paris looks her over. “So, how far has this gone?”

“And what’s that supposed to mean?”

“So, you kissed. Did you tell him you loved him? Did you sleep together?”

Rory turns bright red. “Oh, my god!”

“Apparently that’s a no.”

Rory ducks her head so she doesn’t have to make eye contact. “Look, I told him...I told him I loved him, but that’s it, okay? Now  _ please _ tell me you’re done.”

“Fine, fine.” Paris shakes her head. She starts to walk away, but then something occurs to Rory, so she calls after her. 

“Paris, wait.” The other girl turns around. “You won’t...tell anyone, will you?”

“Who do I look like, Walter Winchell?”

Rory smiles. “Thanks, Paris.”

Paris shrugs, but she’s starting to return the smile. “Hey. What are friends for?” 

**

When the bell rings for lunch, Rory waits outside of the library for Jess. She’s perfectly fine skipping her meal - she had a big breakfast, and the butterflies in her stomach are quelling her appetite. 

Jess makes his way towards her from across the hall, causing her heartbeat to pick up. “Hey.”

“Hey.” He gestures towards the door. “So, shall we start conducting our research?”

“Our research.”

He nods. “Yeah. Our research. You know, in an aisle with books no one ever really reads all the way in the back.”

She grins. “Well, you know how studious I am.”

“Yes, I do.” He offers his hand. “Shall we?”

She takes his hand and laces their fingers together. “Let’s go.”

He leads her through the library to the back, ducking into the very last aisle. The books, as promised, seem very untouched - she wonders how many year’s worth of dust is coating all these books. But then his mouth is on hers and she forgets all about it.

“Jess, wait,” she manages to say, even though the thought of him pulling away is entirely unappealing. He cocks his head to the side.

“What’s up?”   


“I need to be honest with you about something.”

He gestures for her to continue.

Rory sighs, suddenly feeling very guilty. “I know we decided to keep our relationship a secret for a little while, but I got cornered by Paris this morning, and she just started interrogating me, and I swear, I tried to keep it to myself, but she kept pressing and pressing so I...kind of gave in and told her. Sorry,” she adds with a wince.

After a moment, Jess bursts out laughing. 

“What’s so funny?” She asks with a laugh.

He shakes his head. “No, it’s just - Zoey said good morning to me and almost immediately figured it out. And I swear, I said nothing.”

The mention of Zoey brings back bad memories, memories of spiked punch and getting sick in bushes and a killer headache the morning after. Rory pushes past them, reminding herself that Zoey is Jess’ friend, which is a good thing. She’s not going to continue being jealous - or, at least, she’ll try her best. She owes him that much, especially with how he’s handling the Dean situation.

“Well, I guess we’re even then,” she points out.

“I guess we are.” 

“And you’re not mad?”

“I’m not mad,” he reassures her. 

He regards her with reverence for a moment before he smiles and kisses her again. She sighs against his mouth, letting him back her up against the shelves. There’s a little ledge on the self above some cabinets that she leans on as she threads her fingers through his curls and deepens the kiss. 

He kisses her until he hears her every breath, little notes of her voice in each gasp. His hands, resting on her thighs, slide up under her skirt; in response, she moans a little against his mouth, unable to hold it back. 

She loses track of how long it’s been, barely able to focus on anything besides his unrelenting kisses and his hand gripping her thigh and the other one placed on the small of her back. She’s so far gone from reality that when they hear someone clear their throat, it takes her a moment to fully register it.

Jess is a little bit quicker, pulling away from her as if she just burned him. She looks in the direction Jess is, and her stomach drops about twelve stories when she sees who just found them.    
Mr. Medina looks between the two of them, looking more amused than she would’ve thought. “Do I dare ask if you two are skipping class?” He asks, eyebrows raised. 

“It’s - it’s our lunch period,” Rory explains weakly, sure she’s turned beet red. 

He nods. “I should’ve guessed.”

“We were just…” Jess trails off. 

“Looking for a book,” Rory finishes for him, but she doesn’t know why she’s trying. It’s obvious to anyone with sight that they were most definitely  _ not  _ looking for a book. 

“Right,” Mr. Medina says. The look on his face makes her wish the ground would open up and swallow her whole. “A good book?”

Rory and Jess both remain quiet.

“Well, I won’t take up too much of your time,” Mr. Medina continues. “I was just looking for a book myself, right behind you, right...there. Thank you,” he adds as Rory nearly jumps out of the way. “I’ll be going now. Carry on - I mean, no. I’ll...see you two in class.”

“In class,” Jess affirms with a nod. 

Once Mr. Medina is gone, Rory lets out a groan. “Oh, my god. Tell me that did not just happen.”

Jess shrugs, but he’s looking a little flustered himself. “Better than Tristan?”

“That’s a low bar.”

“Fair enough.” Jess exhales slowly before letting out a laugh. “God, we’re never going to live this down, are we?”

“No, we are not,” Rory agrees. “At least he seemed as awkward and embarrassed as us.”

“That’s something.”

“And if we’re looking on the bright side,” Rory continues, “you  _ do  _ look very cute when you’re flustered.”

“Hey, I am not-”

“Your face is all flushed and everything.” She reaches out to stroke his face, but he swats her hand away with a glare. “You’re touchy.”

“Let’s just…” His hands rove down her body before settling on her hips. “Pick up where we left off.”

“I’d be okay with that.”

In a split second, he has her back up against the shelves, but the kiss only lasts a moment before Rory bursts out laughing.

“Come on,” Jess all but whines, but she shakes her head, still shaking with laughter.

“I’m sorry, it’s just - your  _ face,”  _ she teases. “Okay, okay. I’m good now.” He leans in to kiss her again, but she starts giggling again,  _ so  _ unlike her, but she can’t help it.

Jess sighs. “I can wait.”

“You might have to,” she chokes out, wiping her eyes. “Okay. I swear, I’m done. You can kiss me now.”

He gives her a look. “Are you sure?”

“Now who’s dragging this out?”

“Just checking.”

They don’t do much talking after that.

**

At the end of the day, they have their detention. In retrospect, Rory is just relieved that it’s only  _ one  _ \- the incident with Mr. Medina could have been much worse if it had been any other teacher. 

Their detention is with Ms. Tailor. Jess mutters something about being stuck in a math classroom for an hour being added torture, and Rory has to stifle a laugh as Ms. Tailor unlocks her classroom door. She lets them in, and it only takes a few moments for her to get cross when Jess tries to sit at the desk next to Rory. 

“No,” she scolds. “There must be a minimum of two desks between you two. And don’t argue, Mr. Mariano, unless you want it to be  _ two  _ hours of added torture.”

The look on Jess’ face when she says that is priceless. 

Detention, she decides, could be worse. Ms. Tailor lets them work on homework, her nose buried in her lesson plan and textbook. Rory works on her chemistry homework while Jess reads. He claims it’s for his literature class, and while Rory knows for a fact that it is  _ not,  _ Ms. Tailor doesn’t seem to know enough about the Beats to claim otherwise. 

It gets harder to focus, though, as the hour passes. She can feel Jess’ eyes on her, and it doesn’t take long at all for her to begin stealing glances herself. What a picture he makes, with his sleeves rolled up, exposing his forearms, a pen tucked behind his ear, and his hair ruffled in an intentional way, just the way she likes. She loves it, having the freedom to openly admire him without having to feel guilty or having to hide it from him. She’s sixteen and in love with a boy and she doesn’t have to be afraid of it anymore. 

(It’s obvious he feels similarly, and the thought makes her blush.)

She’s sixteen and in love with a boy and while it’s new and strange and different than before, she knows for a fact that it’s worth it even when Ms. Tailor looks up from her work and scolds, “Miss Gilmore, eyes on your work,  _ not  _ on Mr. Mariano.”

**

“As we’re nearing the end of the year,” Mr. Medina says, “we are also nearing our final exams. They will be cumulative - much to your dismay, I’m sure. There will be an in-class essay concerning one of the books we read this semester, and multiple choice questions assessing you on the rest. And there’s no need for groaning, Mr. Dugray. As long as you did your work throughout the semester and you study your notes, you’ll be fine.” There’s a sparkle in his eye, and Rory smiles to herself - it’s clear from his look that Tristan absolutely did  _ not  _ do his work throughout the semester. 

“Are there any questions?” The bell rings, cutting him off. “Alas, we are out of time. Save your questions for tomorrow morning.” He claps his hands together. “Have a good day, folks.”   
As the class files out, Mr. Medina stops Jess before he exits. “Mr. Mariano, can I have a moment before your next class?”

“For old time’s sake?” Jess jokes.

His teacher smiles. “Something like that, I suppose.”

As if it was muscle memory, Jess pulls up a chair and takes a seat in front of Mr. Medina’s desk. Medina sits behind his desk, but there’s no failed paper to take out this time. 

“I just wanted to check up on you,” Mr. Medina explains. “Have you...settled alright? Are you still living with your uncle?”

Jess nods. “Yeah. It’s been - it’s been going well enough.”

“He’s in...Stars Hollow, correct?”

“Yep.”

Mr. Medina nods, a far-away expression on his face for a moment, but it disappears just as quickly. “Well, not to make you uncomfortable or anything, but...I’m proud of you, Jess. You’ve improved greatly since last semester.”

Jess shrugs. “I guess.”

“You’ve been working a lot harder.”

“It’s a low bar, considering my first few essays this year,” Jess quips.

His teacher laughs. “If you want to put it that way. But don’t devalue my words just because it’s praise. Not to mention the stories you’ve been submitting. They’ve been excellent.”

“Yeah, well…” Jess laughs uncomfortably. “I guess it’s...easier, when I’m not living with the before side of Daddy Warbucks.”   


“Oh, I wouldn’t doubt that.”

“Stars Hollow is…” He pauses. “Well, it’s different than New York and Hartford for sure.”   


Mr. Medina nods. “I’ve seen it briefly. Very...odd, but charming.”

“It’s charming until you’re being watched by the entirety of the town all day, every day.”

Mr. Medina chuckles. “It’s that intimate?”

“Try having a meal with your girlfriend in the diner while they all look through the windows.”   


His teacher smiles a bit. “And speaking of...the non-incident yesterday.”

Jess feels his face heat up a bit. “Right.”

“Now, it’s none of my business, of course,” Mr. Medina clarifies, “and I am not going to comment on the two of you. That would be...inappropriate.”

“Right.”

Mr. Medina glances at the clock on the wall. “I think I’ll stop holding you hostage and let you get to your next class. Does that sound good?”

“I definitely don’t need another tardy,” Jess remarks. He stands up, putting the chair back and facing his teacher. “Thank you. For...everything.”

Mr. Medina smiles and nods.

He walks Jess to the door, but before Jess leaves, he says, “Jess, overall, how are you doing? Are things...working out?”

Jess hesitates for a moment. He doesn’t quite believe in jinxes, but he doesn’t want to speak too soon. But even then, he isn’t going to lie to the one teacher who has ever had faith in him. “Yeah. I think for once...I’m actually doing good.”

**

At the end of the day, Rory meets Jess by his locker. He smiles when he sees her leaning up next to it. “This isn’t exactly stealthy, Gilmore.”

“Hey, I wanted to see you before I went home,” Rory says defensively. “And I know it sucks hiding our relationship like this, but until we find out how we’re going to deal with the  _ T _ issue…”

“Hey, I’m just getting my things,” Jess points out. “You were the one who just  _ had  _ to see me.”

She laughs. “I owe you a kiss. Remind me of that later.”

“Oh, you can count on it.”

She shakes her head in mock exasperation. “So, did anyone else find out about us today, or are we capping it at three?”

“I’m hoping I’m one of those three,” Zoey’s voice says from behind Jess. “Or else you might have to kill me. Right? I’ve never seen Fight Club.”

Jess laughs and turns to face his friend. “Why am I not surprised?”

“Rude.”

Rory bites her lip, watching Jess and Zoey awkwardly. She’s resolved to ignore any jealous urges she may have, but she’s realizing now, is harder than she thought - she’s learning now that just because she and Jess are together now, that doesn’t mean she’s immune to jealousy at all. She crosses her arms, folding into herself as she listens. 

“So what’s up?” Jess asks, shutting his locker closed. “What brings you to this end of the hallway?”

“Well,” Zoey begins matter-of-factly, “I wanted to say hi, if that’s allowed these days.”

“Mm, no. Charleston banned that yesterday. Something about annoying blondes cornering guys and their girlfriends unexpectedly.”

“Oh, shut up.” Zoey shakes her head. “But on that note - I’m very happy for you two,” she says, addressing Rory as well. “He’s been pining over you for _months,_ by the way, so I’d say it’s about time you two crazy kids got together.”

“I have not been  _ pining,”  _ Jess objects.

“Pining, yearning, whatever you want to call it, you definitely were.”

“No, I was not.”

“Sure, Frank Sinatra.”

“Oh, don’t listen to her. She’s been a little off ever since they canceled  _ Chicago Hope.” _

Zoey glares at him. “That was a good show, asshole.”   


Rory laughs shakily. “Hey, it was a loss for the culture, right?”

“Exactly!” The other girl exclaims. “See, she gets it!”

Jess shakes his head. “I wouldn’t have let you two meet if I’d known you would gang up on me.”

“He has a thing against hospital shows,” Rory explains. 

“Figures,” Zoey replies. “Jess, are you afraid of needles or something? Or was your uncle killed by a radioactive surgeon?”

“Or were your rich parents shot by a doctor at the opera?”

“We can keep going.”

“All day if we need to.”

Jess gives both of them dark looks as they snicker. “This is  _ not  _ fun for me.”

“Hey, two against one,” Zoey points out. 

“Don’t you have to get home or something?”

“Probably,” Zoey admits. “I’ll see you tomorrow, then?”

“If I must.”

She smiles and shakes her head. “And, uh...you, too, Rory,” she begins to say firmly, but it comes out as more of a question.

“Oh, uh...yeah,” Rory says after a moment, smiling weakly. “Yeah, I’ll see you tomorrow.”

“Good,” Zoey says, sounding relieved. “Bye, you too. Enjoy the honeymoon.”

Jess rolls his eyes as he turns back to Rory. “Hey, you two kinda got along there,” he comments, attempting a casual tone, but there’s a note of hope that she has troubles ignoring. 

“Yeah, I guess,” Rory says. “I - I’m trying,” she admits, and he nods.

“That’s all I’ll ask.”

She wants nothing more than to take his hands in hers, but she holds herself back. “Well, I should probably get home as well.”

Jess nods. “Okay. I’m hanging back for a minute so I can avoid running into you-know-who.”

“Smart.” She adjusts her backpack straps and smiles. “So, I’ll see you back in town.”

“That you will.”

They stand there awkwardly for a moment, lacking a proper way to say goodbye. She wants to kiss him, but there’s a few of their classmates lingering in the hallway, so she settles for a weak wave before she turns and walks away. 

The hiding their relationship thing sounded easy in theory, but as she makes her way towards the exit, she can definitively say that it is  _ not.  _ And yeah, it was more or less her idea, but she has to admit, she hates not being able to kiss him goodbye or, hell, let him drive her home. She has to think of a way to handle Tristan and Dean, and quick. She has a feeling Jess is taking it a lot harder than he’s showing. 

She’s so lost in her thoughts that she doesn’t notice that same blonde boy approaching until he brushes his arm against hers to get her attention. “Hey, Mary.”

“Go away, Tristan,” Rory growls through gritted teeth. She walks a little faster, but he simply follows suit, taking long strides that she knows she can’t escape from.    


“We haven’t really talked in a while, have we?”

“Not since you tried to ‘take me off of Jess’ hands’ when I was drunk at that party.”

“I’m sorry, did I do something to you?”

“Stop it!” She exclaims, stopping in her tracks. “You need to give it up, Tristan. I’m tired of having to fend you off all the time because you can’t just take no for an answer.”

He cocks his head to the side and furrows his brow mockingly. “Well, you’ve never actually said no.”

“So how’s this: no!”

“You didn’t ever give me a chance,” he continues, ignoring her vehement rejection. “Come on. One date.”

“Are you deaf or something? I said  _ no.” _

“Just one date, Mary.”

“No, no, and no. Quit the Xander Harris bit and leave me alone.”

“I have some tickets to a PJ Harvey concert,” he says. “Go with me.”

“Stop.”

“What? You like him, right?”

“PJ Harvey is a  _ woman,”  _ Rory hisses. “And I can’t believe this conversation didn’t end two minutes ago when I told you to leave me alone. Actually, I can, cause you’ve always just been like a fruit fly who just doesn’t go away!”

He holds a hand to his chest in mock offense. “There’s no need for name calling.”

“God, what is your problem?” She demands in disbelief. No matter how long she’s known him, his persistence is always surprising. 

“My  _ problem,” _ Tristan spits, “is that I’ve been nothing but good to you-”

Rory snorts. 

“-and you won’t give me a chance. Come on. Just one, little date at the concert. Who knows, maybe you’ll realize you’re madly in love with me.”

“No, I won’t, and you wanna know why?” She exclaims before she can think it through. “I have never wanted to be with you, Tristan, and guess what? I’m already dating someone, so you can give it up.”

He scoffs. “I thought you broke up with  _ Deano _ at that fundraiser.”

“Not Dean,” she spits. “I’m dating Jess. I’m dating Jess, and I love him, and you never had a chance, so just give it up!”

He blinks at her for a moment. “You’re with Jess.”

“Yes, I am. Now leave me  _ alone.”  _

“What, did he bribe you or something? Or did you lose a bet?” 

She gives him a look. 

“I just don’t get why you’d want  _ him.” _

“I love him, Tristan,” she says evenly. “I’m in love with him. I have been for a while. And I am  _ not  _ going to let you mess up what I have with him, no matter how hard I know you’re going to try. So you might as well just drop it, okay?”

Before he can reply, she storms away from him, leaving him at the entrance to the courtyard, the weight of what she just said dawning on her. She broke her agreement with Jess, broke his trust, even when it was her idea to hide it in the first place. She can only hope she doesn’t find Jess’ body shoved in a locker the next morning, or whatever Tristan might do in retaliation. 

_ At least it can’t get any worse,  _ she thinks to herself.

Maybe she spoke too soon. 

As she turns to face the courtyard, everything comes to a stop when she sees the truck that’s parked in the center of it. Her heart stops when she notices the tall boy leaning up against it, no doubt waiting for her. 

She closes her eyes and takes a deep breath.  _ You got this. _

Rory slowly approaches him, coming to a stop a few feet away. “What are you doing here?”

Dean looks at her, his eyes narrowed and his nostrils flared. “I came here to talk to you, but I can see that you were  _ busy, _ but I know now that I was an idiot to come here.”

She stares at him in disbelief. “What?”

“You were talking to  _ him.” _

Rory glances back to where Dean is nodding at to see Tristan’s retreating form. “Dean, I was not-” She takes a breath. “For the record, I don’t even owe you an explanation, but he was harassing me. I did  _ not  _ want to be talking to him.”

“Right.”

“Dean, what do you want?” She demands impatiently. 

He stares at her as if it should be obvious. “I want you back, Rory.”

She laughs in disbelief. “Jeez, what is with today? First Tristan, now this?” She lets out a deep sigh. “It’s not going to happen.”

“Why not?”

“Because I don’t want to be with you,” she deadpans. “We’re done, Dean. We’ve been done for months. I’ve moved on, I’m  _ happy,  _ and there’s no room in my life for you.”

“Rory, we had something special.”

Rory shakes her head. “No, Dean.  _ You  _ did. I was...I was miserable. I did like you, at first, but I don’t now. Especially not after how you treated me.”

He scoffs. “How  _ I  _ treated  _ you?  _ You were pining over  _ Jess  _ for  _ months.” _

“This isn’t about Jess,” she snaps. “This has always been about you and me and how I don’t want you. I know that now, and I’m not going to let you convince me to give you another chance. You blew it, and now it’s done.”

“So you’re saying you  _ didn’t  _ have feelings for him?”

“Dean-” She swallows. “I did. I do. But that’s not why it ended between us, and you know that.”

“I can’t believe this.”

“What did you think was going to happen, Dean?” She pleads. “That I’d forgive you and you’d sweep me off my feet? That there would be some cinematic reunion? Because that’s not on the table. You might not like it, but I’m in love with Jess, and that’s not going to change. No matter how much you want it to.”

He stares at her in silence for a moment. “Just tell me this,” he says finally. “Why him?”

She shakes her head. “It’s him because I would never have to go through this with him. It’s him because even after everything, he’s still here. You bailed when the going got tough, but he’s still here.” She smiles. “Goodbye, Dean.” And with that, she walks away.

Rory can’t help but smile to herself as she hurries back the way she came, entering the hallway and picking up the pace. There’s a sense of finality taking her over, of closure, of loose ends being tied. It’s over. It’s done. It’s a chapter closed and another one open, and she couldn’t be any more relieved. 

She sees him, leaning up against his locker and reading, holding his book in that weird way she likes to give him a hard time for. She speeds up, dropping her bag on the floor once she reaches him.

He looks up from his book. “Hey, what are y-”

She catches him off guard by grabbing his face and kissing him firmly on the mouth. He drops his book in surprise, but quickly catches on, kissing her back with just as much fervor, his hands on the small of her back.

Eventually, she pulls away, breathing heavily. He looks at her, puzzled. “What was that for?”

“No reason,” she breathes, unable to continue her grin. “Just...because.”

“Good enough reason for me,” he murmurs. “But what about-”

She shakes her head. “I don’t care. He can do whatever he wants. It doesn’t matter as long as I’ve got you.”

“Are you sure?”

“Yes.”

“What happened in the last ten minutes that made you decide that-”

“I’ll explain later,” she says, “I promise. Okay?”

“Okay,” he replies with a chuckle, “but I still don’t-”

She cuts him off and kisses him again.

**

They make out for a little by the lockers before he drives her home.

**

The next week or so goes by surprisingly smoothly. Her conversation with Dean seems to have had some impact, because besides the handful of death glares she caught him giving Jess during the town meeting, he hasn’t said a word to either of them. Same goes for Tristan, too; she hasn’t even seen him around school. 

One afternoon after the final bell, Rory finally sees him. She’s walking hand in hand with Jess towards the parking lot when the other boy approaches them. She glances over at Jess, the same worried expression on both of their faces.

“We need to talk,” Tristan begins, catching them both off guard.

Jess eyes his former step-brother suspiciously. “Can this wait?”

“No, it can’t,” Tristan says in an uncharacteristically subdued tone. “As of today, I am no longer a student at Chilton, so this kind of has to be done now.”

Rory blinks at him in shock. “What?”

“My father had me pulled out of school.”

Jess and Rory exchange another surprised glance, which makes Tristan roll his eyes. 

“Cut that out, would you? It’s annoying.”

“Why are you telling us?” Rory asks. “I mean, why not just leave and let us wonder what happened?”

“I don’t know, and I’m kind of regretting this decision right now anyway, so let’s just make this quick, okay?”

Jess sighs. “Fine. So what happened?”

“He’s sending me to military school.”

“Military school?” Rory and Jess both exclaim at the same time.

He nods. “Yep. Norwich University up in Vermont.”

Rory stares at him, unsure what to say. “But why now, all of a sudden?”

“Just...got in some trouble, okay?” Tristan answers her impatiently. “It doesn’t matter what. I’m just telling you guys now, but just wait a few minutes before you start celebrating, would you?”

Jess snorts. “What, are you gonna miss this place or something?”

“Trust me, I’m glad to be getting as far away from you as possible,” Tristan retorts. “Can’t pretend that it’s always been my dream to go to military school, but whatever gets me out of here.”

“Well...good luck,” Rory supplies, uncertain of how much she really means it. She’s never seen any vulnerability in him before, and she’s unsure of how to react. 

“Thanks. I guess.” Tristan looks to Jess. “What? Not gonna say anything?”

“Figured I’d keep the moment as pleasant as possible by keeping my mouth shut.”

“Good thinking,” Tristan says. “I hate agreeing with you, so this is...goodbye, then.”

“Bye,” Rory offers weakly. The blonde boy nods curtly at the two of them before he walks through the iron gates towards a big black car.

As it drives away, Rory finds herself wondering what’ll become of him, if she’ll ever see him again. She’s not exactly keen on the idea, but despite how much she hates him, she still hopes he’ll turn out alright. Her mom would say it’s blind optimism, and Jess probably would too, and maybe they’d be right - but she’d rather believe there’s a little bit of good in everyone than spend the rest of her life hating the memory of someone she doesn’t know.

She looks over at Jess and smiles. “Should we go?”

He nods. “I’m not particularly feeling the urge to mourn.”

She laughs. “Alright. Then let’s go home.”

**

That night, Lorelai has a surge in energy and decides to start spring cleaning. She loses steam about halfway through, very conveniently when it’s time to organize everything they decided to keep. Rory threatens to throw out her mom’s favorite jean jacket if she doesn’t keep working as she makes her way to the front hall closet. As she weeds through the coats, she catches a glimpse of a cardboard box. She manages to pull it out, surprised when she realizes it’s the Jess box she had put together after he’d moved to Stars Hollow.

“I’ll be right back,” she calls out to her mom, carrying the box to her bedroom.

“Fine. But come back soon before I drown in this sea of trash bags!”

Rory shuts her bedroom door behind her, sitting down on her bed with the box. She pulls out  _ The Tell-Tale Heart  _ and smiles to herself. There’s a lot of memories in this box, ones that aren’t so painful, not anymore.

Rory reaches in and takes out the copy of  _ High Fidelity  _ she’d put in there before getting up and shelving them in their respective spots on her bookshelf. She continues to take things out of the box, putting each item back where they belong until the box is empty.

When she’s done, she looks around her room, feeling an odd sense of nostalgia that she can’t quite explain. But the past is the past, and she has to admit, it’s a good feeling - now that everything is fixed, even their worst moments aren’t so bad to remember anymore.

**

The rest of the school year goes by in a blur. It’s a whirlwind of projects, essays, finals until suddenly, it’s over, and there’s only one day left of sophomore year.

Luke insists on driving Jess to school that day, claiming that it’s an important moment as Jess’ uncle to witness, even though Jess knows it’s a load of bs - but his uncle will gladly take the excuse to pinch his cheek and mockingly coo about just how far he’s come. 

“You got everything?”

“For the millionth time, yes, I have all the nothing I need for the last day of school,” Jess groans. “Can I go now, or do you want me to be late?”

“Fine, fine,” Luke concedes. “You and Rory taking the bus home?”

“Well, I would’ve been able to drive, if you hadn’t insisted on driving me here.”

“What are you talking about? Your car’s been in the shop for a month.”

Jess sighs. “Wishful thinking.” 

He unbuckles and climbs out of the car, but before he walks away, Luke speaks. “Have, uh, have a good last day, Jess.”

Jess blinks at him in surprise. “Thanks.”

Luke nods in response.

Jess shuts the car door and walks towards the iron gates where Rory is waiting for him. She smiles, takes his hand, and the two of them walk through the entrance, ready for the day ahead of them. 


End file.
